Isoxazolines for controlling invertebrate pests

ABSTRACT

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, 
     
       
         
         
             
             
         
       
     
     wherein
         A 1 , A 2 , A 3 , A 4 , A 5  and A 6  are independently selected from the group consisting of CR 3  and N; provided that at most 3 of A 1 , A 2 , A 3 , A 4 , A 5  and A 6  is N;   B 1 , B 2  and B 3  are independently selected from the group consisting of CR 2  and N;   each R 3  is independently H, halogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkoxy, C 1 -C 6  alkylthio, C 1 -C 6  haloalkylthio, C 1 -C 6  alkylsulfinyl, C 1 -C 6  haloalkylsulfinyl, C 1 -C 6  alkylsulfonyl, C 1 -C 6  haloalkylsulfonyl, C 1 -C 6  alkylamino, C 2 -C 6  dialkylamino, —CN or —NO 2 ; and R 1 , R 2 , R 4 , R 5 , W and n are as defined in the disclosure.
 
Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain isoxazolines, their N-oxides, saltsand compositions suitable for agronomic and nonagronomic uses, includingthose uses listed below, and methods of their use for controllinginvertebrate pests such as arthropods in both agronomic and nonagronomicenvironments.

BACKGROUND OF THE INVENTION

The control of invertebrate pests is extremely important in achievinghigh crop efficiency. Damage by invertebrate pests to growing and storedagronomic crops can cause significant reduction in productivity andthereby result in increased costs to the consumer. The control ofinvertebrate pests in forestry, greenhouse crops, ornamentals, nurserycrops, stored food and fiber products, livestock, household, turf, woodproducts, and public and animal health is also important. Many productsare commercially available for these purposes, but the need continuesfor new compounds that are more effective, less costly, less toxic,environmentally safer or have different modes of action.

PCT Patent Publication WO 05/085216 discloses isoxazoline derivatives ofFormula i as insecticides

wherein, inter alia, each of A¹, A² and A³ are independently C or N; Gis a benzene ring; W is O or S; and X is halogen or C₁-C₆ haloalkyl.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 including allgeometric and stereoisomers, N-oxides, and salts thereof, andcompositions containing them and their use for controlling invertebratepests:

wherein

-   -   A¹, A², A³, A⁴, A⁵ and A⁶ are independently selected from the        group consisting of CR³ and N, provided that at most 3 of A¹,        A², A³, A⁴, A⁵ and A⁶ are N;    -   B¹, B² and B³ are independently selected from the group        consisting of CR² and N;    -   W is O or S;    -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more substituents        independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,        C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN        or —NO₂;    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        —CN or —NO₂;    -   R⁴ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   R⁵ is H, OR¹⁰, NR¹¹R¹² or Q¹; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷; or    -   R⁴ and R⁵ are taken together with the nitrogen to which they are        attached to form a ring containing 2 to 6 atoms of carbon and        optionally one additional atom selected from the group        consisting of N, S and O, said ring optionally substituted with        1 to 4 substituents independently selected from the group        consisting of C₁-C₂ alkyl, halogen, —CN, —NO₂ and C₁-C₂ alkoxy;    -   each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂;    -   each R⁷ is independently halogen, C₁-C₆ alkyl, C₃-C₆ cycloalkyl,        C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₃-C₆        cycloalkylamino, C₂-C₇ alkylcarbonyl, C₂-C₇ alkoxycarbonyl,        C₂-C₇ alkylaminocarbonyl, C₃-C₉ dialkylaminocarbonyl, C₂-C₇        haloalkylcarbonyl, C₂-C₇ haloalkoxycarbonyl, C₂-C₇        haloalkylaminocarbonyl, C₃-C₉ halodialkylaminocarbonyl, hydroxy,        —NH₂, —CN or —NO₂; or Q²;    -   each R⁸ is independently halogen, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        C₂-C₄ alkoxycarbonyl, —CN or —NO₂;    -   each R⁹ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        —CN, —NO₂, phenyl or pyridinyl;    -   R¹⁰ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more halogen;    -   R¹¹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   R¹² is H; Q³; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷; or    -   R¹¹ and R¹² are taken together with the nitrogen to which they        are attached to form a ring containing 2 to 6 atoms of carbon        and optionally one additional atom selected from the group        consisting of N, S and O, said ring optionally substituted with        1 to 4 substituents independently selected from the group        consisting of C₁-C₂ alkyl, halogen, —CN, —NO₂ and C₁-C₂ alkoxy;    -   Q¹ is a phenyl ring, a 5- or 6-membered heterocyclic ring, or an        8-, 9- or 10-membered fused bicyclic ring system optionally        containing one to three heteroatoms selected from up to 1 O, up        to 1 S and up to 3 N, each ring or ring system optionally        substituted with one or more substituents independently selected        from R⁸;    -   each Q² is independently a phenyl ring or a 5- or 6-membered        heterocyclic ring, each ring optionally substituted with one or        more substituents independently selected from R⁹;    -   Q³ is a phenyl ring or a 5- or 6-membered heterocyclic ring,        each ring optionally substituted with one or more substituents        independently selected from R⁹; and    -   n is 0, 1 or 2.

This invention also provides a composition comprising a compound ofFormula 1, an N-oxide or a salt thereof, and at least one additionalcomponent selected from the group consisting of a surfactant, a soliddiluent and a liquid diluent. In one embodiment, this invention alsoprovides a composition for controlling an invertebrate pest comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, and at least one additional component selected from thegroup consisting of a surfactant, a solid diluent and a liquid diluent,said composition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent.

This invention further provides a spray composition for controlling aninvertebrate pest comprising a biologically effective amount of acompound of Formula 1, an N-oxide or a salt thereof, or the compositiondescribed above and a propellant. This invention also provides a baitcomposition for controlling an invertebrate pest comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, or the composition described in the embodiment above,one or more food materials, optionally an attractant, and optionally ahumectant.

This invention further provides a trap device for controlling aninvertebrate pest comprising said bait composition and a housing adaptedto receive said bait composition, wherein the housing has at least oneopening sized to permit the invertebrate pest to pass through theopening so the invertebrate pest can gain access to said baitcomposition from a location outside the housing, and wherein the housingis further adapted to be placed in or near a locus of potential or knownactivity for the invertebrate pest.

This invention also provides a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of Formula 1, an N-oxideor a salt thereof, (e.g., as a composition described herein). Thisinvention also relates to such method wherein the invertebrate pest orits environment is contacted with a composition comprising abiologically effective amount of a compound of Formula 1, an N-oxide ora salt thereof, and at least one additional component selected from thegroup consisting of a surfactant, a solid diluent and a liquid diluent,said composition optionally further comprising a biologically effectiveamount of at least one additional biologically active compound or agent.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains” or “containing,” or any othervariation thereof, are intended to cover a non-exclusive inclusion. Forexample, a composition, a mixture, process, method, article, orapparatus that comprises a list of elements is not necessarily limitedto only those elements but may include other elements not expresslylisted or inherent to such composition, mixture, process, method,article, or apparatus. Further, unless expressly stated to the contrary,“or” refers to an inclusive or and not to an exclusive or. For example,a condition A or B is satisfied by any one of the following: A is true(or present) and B is false (or not present), A is false (or notpresent) and B is true (or present), and both A and B are true (orpresent).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to in this disclosure, the term “invertebrate pest” includesarthropods, gastropods and nematodes of economic importance as pests.The term “arthropod” includes insects, mites, spiders, scorpions,centipedes, millipedes, pill bugs and symphylans. The term “gastropod”includes snails, slugs and other Stylommatophora. The term “helminths”includes worms in the phylum of Nemathelminth, Platyhelminth andAcanthocephala such as: round worms, heartworms, and phytophagousnematodes (Nematoda), flukes (Trematoda), tape worms (Cestoda) andthrony-headed worms.

In the context of this disclosure “invertebrate pest control” meansinhibition of invertebrate pest development (including mortality,feeding reduction, and/or mating disruption), and related expressionsare defined analogously.

The term “agronomic” refers to the production of field crops such as forfood and fiber and includes the growth of corn, soybeans and otherlegumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize),leafy vegetables (e.g., lettuce, cabbage, and other cole crops),fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers andcucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g.,pome, stone and citrus), small fruit (berries, cherries) and otherspecialty crops (e.g., canola, sunflower, olives). The term“nonagronomic” refers to other horticultural crops (e.g., greenhouse,nursery or ornamental plants not grown in a field), residential andcommercial structures in urban and industrial settings, turf (e.g., sodfarm, pasture, golf course, residential lawn, recreational sports field,etc.), wood products, stored product, agro-forestry and vegetationmanagement, public health (human) and animal health (e.g., domesticatedanimals such as pets, livestock and poultry, undomesticated animals suchas wildlife) applications.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkylthio” includes branched or straight-chain alkylthio moieties suchas methylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylamino”, “dialkylamino”,and the like, are defined analogously to the above examples.“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C—, ClCH₂—, CF₃CH₂— and CF₃CCl₂—. The terms“halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, and the like, aredefined analogously to the term “haloalkyl”. Examples of “haloalkoxy”include CF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of“haloalkylthio” include CCl₃S—, CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—.Examples of “haloalkylsulfinyl” include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)—and CF₃CF₂S(O)—. Examples of “haloalkylsulfonyl” include CF₃S(O)₂—,CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃C(═O)—, CH₃CH₂OC(═O), CH₃CH₂CH₂C(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 8. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄alkoxyalkyl designates the various isomers of an alkyl group substitutedwith an alkoxy group containing a total of four carbon atoms, examplesincluding CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., (R²)_(n), n is 1, 2, 3, 4 or 5.When a group contains a substituent which can be hydrogen, for exampleR², then when this substituent is taken as hydrogen, it is recognizedthat this is equivalent to said group being unsubstituted.

The term “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denotes rings or ring systems in which at least one ring atom isnot carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclicring contains no more than 4 nitrogens, no more than 2 oxygens and nomore than 2 sulfurs. The heterocyclic ring can be attached through anyavailable carbon or nitrogen by replacement of hydrogen on said carbonor nitrogen. The heterocyclic ring can be a saturated, partiallyunsaturated, or fully unsatuturated ring. When a fully unsaturatedheterocyclic ring satisfies the Hückel rule, then said ring is alsocalled a “heteroaromatic ring” or “aromatic heterocyclic ring”.

The term “aromatic ring” or “aromatic ring system” denotes fullyunsaturated carbocycles and heterocycles in which at least one ring ofthe polycyclic ring system is aromatic (where aromatic indicates thatthe Hückel rule is satisfied for the ring system). The term “fusedbicyclic ring system” includes a ring system comprised of two fusedrings in which either ring can be saturated, partially unsaturated, orfully unsatuturated. The term “fused heterobicyclic ring system”includes a ring system comprised of two fused rings in which at leastone ring atom is not carbon and can be aromatic or non aromatic, asdefined above.

The term “optionally substituted” in connection with the heterocyclicrings refers to groups which are unsubstituted or have at least onenon-hydrogen substituent that does not extinguish the biologicalactivity possessed by the unsubstituted analog. As used herein, thefollowing definitions shall apply unless otherwise indicated. The term“optionally substituted” is used interchangeably with the phrase“substituted or unsubstituted” or with the term “(un)substituted.”Unless otherwise indicated, an optionally substituted group may have asubstituent at each substitutable position of the group, and eachsubstitution is independent of the other.

When Q¹ is a 5- or 6-membered nitrogen-containing heterocyclic ring, itmay be attached to the remainder of Formula 1 though any availablecarbon or nitrogen ring atom, unless otherwise described. Similarly,when Q² or Q³ is a 5- or 6-membered nitrogen-containing heterocycle, itmay be attached through any available carbon or nitrogen ring atom,unless otherwise described.

As noted above, Q¹, Q² or Q³ can be (among others) phenyl optionallysubstituted with one or more substituents selected from a group ofsubstituents as defined in the Summary of Invention. An example ofphenyl optionally substituted with one to five substituents is the ringillustrated as U-1 in Exhibit 1, wherein R^(v) is R⁸ or R⁹ as defined inthe Summary of the Invention for Q¹, Q² or Q³ and r is an integer from 0to 5.

As noted above, Q¹, Q² or Q³ can be (among others) 5- or 6-memberedheterocyclic ring, which may be saturated or unsaturated, optionallysubstituted with one or more substituents selected from a group ofsubstituents as defined in the Summary of Invention. Examples of a 5- or6-membered unsaturated aromatic heterocyclic ring optionally substitutedwith from one or more substituents include the rings U-2 through U-61illustrated in Exhibit 1 wherein R^(v) is any substituent as defined inthe Summary of the Invention for Q¹, Q² or Q³ (i.e. R⁸ or R⁹) and r isan integer from 0 to 4.

Exhibit 1

Note that when Q¹, Q² or Q³ is a 5- or 6-membered saturated orunsaturated non-aromatic heterocyclic ring optionally substituted withone or more substituents selected from the group of substituents asdefined in the Summary of Invention for Q¹, Q² or Q³, one or two carbonring members of the heterocycle can optionally be in the oxidized formof a carbonyl moiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturatedheterocyclic ring include the rings G-1 through G-35 as illustrated inExhibit 2. Note that when the attachment point on the G group isillustrated as floating, the G group can be attached to the remainder ofFormula 1 through any available carbon or nitrogen of the G group byreplacement of a hydrogen atom. The optional substituents can beattached to any available carbon or nitrogen by replacing a hydrogenatom.

Note that when Q¹, Q² or Q³ comprises a ring selected from G-28 throughG-35, G² is selected from O, S or N. Note that when G² is N, thenitrogen atom can complete its valence by substitution with either H orthe substituents as defined in the Summary of Invention for Q¹, Q² or Q³(i.e. R⁸ or R⁹).

Exhibit 2

As noted above, Q¹ can be (among others) an 8-, 9- or 10-membered fusedbicyclic ring system optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of Invention (i.e. R⁸). Examples of 8-, 9- or 10-membered fusedbicyclic ring system optionally substituted with from one or moresubstituents include the rings U-81 through U-123 illustrated in Exhibit3 wherein R^(v) is any substituent as defined in the Summary of theInvention for Q¹ (i.e. R⁸) and r is an integer from 0 to 4.

Exhibit 3

Although R^(v) groups are shown in the structures U-1 through U-123, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H when attached to an atom, thisis the same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers or as an opticallyactive form.

One skilled in the art will appreciate that not all nitrogen containingheterocyclic rings can form N-oxides since the nitrogen requires anavailable lone pair for oxidation to the oxide; one skilled in the artwill recognize those nitrogen containing heterocyclic rings which canform N-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine or triethylamine) orinorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium,potassium, lithium, calcium, magnesium or barium) when the compoundcontains an acidic moiety such as when R⁴ is alkylcarbonyl and R⁵ is H.

Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include:

Embodiment 1

-   -   A compound of Formula 1 wherein R¹ is C₁-C₃ alkyl optionally        substituted with one or more substituents independently selected        from R⁶.

Embodiment 2

-   -   A compound of Embodiment 1 wherein R¹ is C₁-C₃ alkyl optionally        substituted with halogen.

Embodiment 3

-   -   A compound of Embodiment 2 wherein R¹ is C₁-C₃ alkyl substituted        with halogen.

Embodiment 4

-   -   A compound of Embodiment 3 wherein R¹ is C₁-C₃ alkyl substituted        with F.

Embodiment 5

-   -   A compound of Embodiment 4 wherein R¹ is C₁-C₃ alkyl fully        substituted with F.

Embodiment 6

-   -   A compound of Embodiment 5 wherein R¹ is CF₃.

Embodiment 7

-   -   A compound of Formula 1 wherein each R² is independently H,        halogen, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy or —CN.

Embodiment 8

-   -   A compound of Embodiment 7 wherein each R² is independently H,        CF₃, OCF₃, halogen or —CN.

Embodiment 9

-   -   A compound of Embodiment 7 wherein each R² is independently        halogen or C₁-C₃ haloalkyl.

Embodiment 10

-   -   A compound of Formula 1 wherein each R³ is independently H,        halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆        halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, —CN or —NO₂.

Embodiment 11

-   -   A compound of Embodiment 10 wherein each R³ is independently H,        C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy or        —CN.

Embodiment 12

-   -   A compound of Embodiment 11 wherein each R³ is independently H,        C₁-C₄ alkyl or —CN.

Embodiment 13

-   -   A compound of Embodiment 12 wherein each R³ is H.

Embodiment 14

-   -   A compound of Formula 1 wherein R⁴ is H, C₁-C₆ alkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl.

Embodiment 15

-   -   A compound of Embodiment 14 wherein R⁴ is H.

Embodiment 16

-   -   A compound of Formula 1 wherein R⁵ is H, OR¹⁰, NR¹¹R¹² or Q¹; or        C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₄ cycloalkyl,        C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each optionally        substituted with one or more substituents independently selected        from R⁷.

Embodiment 17

-   -   A compound of Embodiment 16 wherein R⁵ is H; or C₁-C₄ alkyl,        C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₄ cycloalkyl, C₄-C₇        alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each optionally        substituted with one or more substituents independently selected        from R⁷.

Embodiment 18

-   -   A compound of Embodiment 17 wherein R⁵ is H; or C₁-C₄ alkyl        optionally substituted with one or more substituents        independently selected from R⁷.

Embodiment 19

-   -   A compound of Embodiment 18 wherein R⁵ is C₁-C₄ alkyl optionally        substituted with one or more substituents independently selected        from R⁷.

Embodiment 20

-   -   A compound of Embodiment 19 wherein R⁵ is CH₂CF₃.

Embodiment 21

-   -   A compound of Embodiment 19 wherein R⁵ is CH₂-2-pyridinyl.

Embodiment 22

-   -   A compound of Embodiment 16 wherein R⁵ is OR¹⁰, NR¹¹R¹² or Q¹.

Embodiment 23

-   -   A compound of Embodiment 22 wherein R⁵ is NR¹¹R¹²

Embodiment 24

-   -   A compound of Embodiment 22 wherein R⁵ is Q¹.

Embodiment 25

-   -   A compound of Formula 1 wherein R⁶ is halogen.

Embodiment 26

-   -   A compound of Formula 1 wherein each R⁷ is independently        halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄        alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkylcarbonyl, C₂-C₄        alkoxycarbonyl, C₂-C₅ alkylaminocarbonyl, C₂-C₅        haloalkylcarbonyl, C₂-C₅ haloalkoxycarbonyl, C₂-C₅        haloalkylaminocarbonyl, —NH₂, —CN or —NO₂; or Q².

Embodiment 27

-   -   A compound of Embodiment 26 wherein each R⁷ is independently        halogen, C₂-C₄ alkoxycarbonyl, C₂-C₅ alkylaminocarbonyl, C₂-C₅        haloalkoxycarbonyl, C₂-C₅ haloalkylaminocarbonyl, —NH₂, —CN or        —NO₂; or Q².

Embodiment 28

-   -   A compound of Embodiment 27 wherein each R⁷ is independently        halogen, C₂-C₅ alkylaminocarbonyl, C₂-C₅ haloalkylaminocarbonyl        or Q².

Embodiment 29

-   -   A compound of Embodiment 28 wherein each R⁷ is independently        halogen or Q².

Embodiment 30

-   -   A compound of Embodiment 29 wherein each R⁷ is independently F,        Cl or Br.

Embodiment 31

-   -   A compound of Embodiment 30 wherein each R⁷ is F.

Embodiment 32

-   -   A compound of Embodiment 29 wherein each R⁷ is Q².

Embodiment 33

-   -   A compound of Formula 1 wherein each R⁸ is independently        halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl or —CN.

Embodiment 34

-   -   A compound of Formula 1 wherein each R⁹ is halogen, C₁-C₄ alkyl,        C₁-C₄ haloalkyl, —CN, phenyl or pyridinyl.

Embodiment 35

-   -   A compound of Formula 1 wherein R¹⁰ is H; or C₁-C₆ alkyl        optionally substituted with one or more halogen.

Embodiment 36

-   -   A compound of Formula 1 wherein R¹¹ is H, C₁-C₆ alkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl.

Embodiment 37

-   -   A compound of Embodiment 34 wherein R¹¹ is H.

Embodiment 38

-   -   A compound of Formula 1 wherein R¹² is H or Q³; or C₁-C₄ alkyl        optionally substituted with one or more substituents        independently selected from R⁷.

Embodiment 39

-   -   A compound of Formula 1 wherein Q¹ is phenyl, pyridinyl,        thiazolyl,

-   -   -   each optionally substituted with one or more substituents            independently selected from R⁸.

Embodiment 40

-   -   A compound of Formula 1 wherein each Q² is independently phenyl,        pyridinyl or thiazolyl, each optionally substituted with one or        more substituents independently selected from R⁹.

Embodiment 41

-   -   A compound of Embodiment 34 wherein each Q² is independently        phenyl, pyridinyl or thiazolyl.

Embodiment 42

-   -   A compound of Formula 1 wherein Q³ is phenyl, pyridinyl or        thiazolyl, each optionally substituted with one or more        substituents independently selected from R⁹.

Embodiment 43

-   -   A compound of Formula 1 wherein A¹, A² and A⁶ are A⁴, A³, A², A³        A⁴, A⁵ each CR³.

Embodiment 44

-   -   A compound of Formula 1 wherein A¹ is N; and A², A³, A⁴, A⁵ and        A⁶ are each CR³.

Embodiment 45

-   -   A compound of Formula 1 wherein A² is N; and A¹, A³, A⁴, A⁵ and        A⁶ are each CR³.

Embodiment 46

-   -   A compound of Formula 1 wherein A⁴ is N; and A¹, A², A³, A⁵ and        A⁶ are each CR³.

Embodiment 47

-   -   A compound of Formula 1 wherein A⁶ is N; and A¹, A², A³, A⁴ and        A⁵ are each CR³.

Embodiment 48

-   -   A compound of Formula 1 wherein B¹, B² and B³ are independently        CR².

Embodiment 49

-   -   A compound of Embodiment 48 wherein B² is CH.

Embodiment 50

-   -   A compound of Formula 1 wherein B¹ is N; and B² and B³ are        independently CR².

Embodiment 51

-   -   A compound of Formula 1 wherein B² is N; and B¹ and B³ are        independently CR².

Embodiment 52

-   -   A compound of Formula 1 wherein B² is CR²; and B¹ and B³ are N.

Embodiment 53

-   -   A compound of Formula 1 wherein W is O.

Embodiment 54

-   -   A compound of Formula 1 wherein n is 0.

Embodiments of this invention, including Embodiments 1-54 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds. In addition, embodiments of this invention,including Embodiments 1-54 above as well as any other embodimentsdescribed herein, and any combination thereof, pertain to thecompositions and methods of the present invention.

Combinations of Embodiments 1-54 are illustrated by:

Embodiment A

-   -   A compound of Formula 1 wherein        -   R¹ is C₁-C₃ alkyl optionally substituted with one or more            substituents independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ haloalkyl, C₁-C₆        haloalkoxy or —CN; and    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, —CN or —NO₂.

Embodiment B

-   -   A compound of Embodiment A wherein        -   B¹, B² and B³ are independently CR²;        -   W is O;        -   R⁴ is H, C₁-C₆ alkyl, C₂-C₇ alkylcarbonyl or C₂-C₇            alkoxycarbonyl; and        -   R⁵ is H, NR¹¹R¹² or Q¹; or C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄            alkynyl, C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇            cycloalkylalkyl, each optionally substituted with one or            more substituents independently selected from R⁷.

Embodiment C

-   -   A compound of Embodiment B wherein        -   R¹ is C₁-C₃ alkyl optionally substituted with halogen;    -   each R² is independently H, CF₃, OCF₃, halogen or —CN;    -   each R³ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₃-C₆        cyclopropyl, C₁-C₄ alkoxy or —CN; and    -   each R⁷ is independently halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy,        C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄        alkylcarbonyl, C₂-C₄ alkoxycarbonyl, C₂-C₅ alkylaminocarbonyl,        C₂-C₅ haloalkylcarbonyl, C₂-C₅ haloalkoxycarbonyl, C₂-C₅        haloalkylaminocarbonyl, —NH₂, —CN or —NO₂; or Q².

Embodiment D

-   -   A compound of Embodiment C wherein        -   R⁴ is H;        -   R⁵ is C₁-C₄ alkyl optionally substituted with one or more            substituents independently selected from R⁷;    -   each R⁷ is independently halogen or Q²; and    -   each Q² is independently phenyl, pyridinyl or thiazolyl.

Embodiment E

-   -   A compound of Embodiment D wherein        -   R¹ is CF₃;        -   A¹, A², A³, A⁴, A⁵ and A⁶ are each CR³;        -   B² is CR²; and    -   each R³ is independently H, C₁-C₄ alkyl or —CN.

Embodiment F

-   -   A compound of Embodiment E wherein        -   B² is CH;    -   each R² is independently halogen or C₁-C₃ haloalkyl;        -   R³ is H;        -   R⁵ is CH₂CF₃ or CH₂-2-pyridinyl; and        -   n is 0.

Specific embodiments include compounds of Formula 1 selected from thegroup consisting of:

-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarbothioamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-ethyl-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-methoxyethyl)-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(2,2,2-trifluoroethyl)-2-oxoethyl]-1-naphthalenecarboxamide,-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-quinolinecarboxamide,-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-isoquinolinecarboxamide,    and-   1-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-isoquinolinecarboxamide.

Of note are specific embodiments include compounds of Formula 1 selectedfrom the group consisting of:

-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamide,-   4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarbothioamide,-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-quinolinecarboxamide,-   5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-isoquinolinecarboxamide,    and-   1-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-isoquinolinecarboxamide.

Further specific embodiments include any combination of the compounds ofFormula 1 selected from the group immediately above.

Embodiments of the present invention further include:

Embodiment AA A compound of Formula 1q, an N-oxide, or a salt thereof,

wherein

-   -   A¹, A², A³, A⁴, A⁵ and A⁶ are independently selected from the        group consisting of CR³ and N, provided that at most 3 of A¹,        A², A³, A⁴, A⁵ and A⁶ are N;    -   W is O or S;    -   R¹ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more substituents        independently selected from R⁶;    -   each R² is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio,        C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN        or —NO₂;    -   each R³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        —CN or —NO₂;    -   R⁴ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   R⁵ is H, OR¹⁰, NR¹¹R¹² or Q¹; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷; or    -   R⁴ and R⁵ are taken together with the nitrogen to which they are        attached to form a ring containing 2 to 6 atoms of carbon and        optionally one additional atom selected from the group        consisting of N, S and O, said ring optionally substituted with        1 to 4 substituents independently selected from the group        consisting of C₁-C₂ alkyl, halogen, —CN, —NO₂ and C₁-C₂ alkoxy;    -   each R⁶ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, —CN        or —NO₂;    -   each R⁷ is independently halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy,        C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₇        alkylcarbonyl, C₂-C₇ alkoxycarbonyl, C₂-C₇ alkylaminocarbonyl,        C₃-C₉ dialkylaminocarbonyl, C₂-C₇ haloalkylcarbonyl, C₂-C₇        haloalkoxycarbonyl, C₂-C₇ haloalkylaminocarbonyl, C₃-C₉        halodialkylaminocarbonyl, hydroxy, —NH₂, —CN or —NO₂; or Q²;    -   each R⁸ is independently halogen, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        C₂-C₄ alkoxycarbonyl, —CN or —NO₂;    -   each R⁹ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,        —CN, —NO₂, phenyl or pyridinyl;    -   R¹⁰ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, each        optionally substituted with one or more halogen;    -   R¹¹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆        cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl, C₂-C₇        alkylcarbonyl or C₂-C₇ alkoxycarbonyl;    -   R¹² is H; Q³; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇        cycloalkylalkyl, each optionally substituted with one or more        substituents independently selected from R⁷; or    -   R¹¹ and R¹² are taken together with the nitrogen to which they        are attached to form a ring containing 2 to 6 atoms of carbon        and optionally one additional atom selected from the group        consisting of N, S and O, said ring optionally substituted with        1 to 4 substituents independently selected from the group        consisting of C₁-C₂ alkyl, halogen, —CN, —NO₂ and C₁-C₂ alkoxy;    -   Q¹ is a phenyl ring, a 5- or 6-membered heterocyclic ring, or an        8-, 9- or 10-membered fused bicyclic ring system optionally        containing one to three heteroatoms selected from up to 1 O, up        to 1 S and up to 3 N, each ring or ring system optionally        substituted with one or more substituents independently selected        from R⁸;    -   each Q² is independently a phenyl ring or a 5- or 6-membered        heterocyclic ring, each ring optionally substituted with one or        more substituents independently selected from R⁹;    -   Q³ is a phenyl ring or a 5- or 6-membered heterocyclic ring,        each ring optionally substituted with one or more substituents        independently selected from R⁹; and    -   n″ is 1, 2, 3, 4 or 5.

Of note is that compounds of this invention are characterized byfavorable metabolic and/or soil residual patterns and exhibit activitycontrolling a spectrum of agronomic and nonagronomic invertebrate pests.

Of particular note, for reasons of invertebrate pest control spectrumand economic importance, protection of agronomic crops from damage orinjury caused by invertebrate pests by controlling invertebrate pestsare embodiments of the invention. Compounds of this invention because oftheir favorable translocation properties or systemicity in plants alsoprotect foliar or other plant parts which are not directly contactedwith a compound of Formula 1 or a composition comprising the compound.

Also noteworthy as embodiments of the present invention are compositionscomprising a compound of any of the preceding Embodiments, as well asany other embodiments described herein, and any combinations thereof,and at least one additional component selected from the group consistingof a surfactant, a solid diluent and a liquid diluent, said compositionsoptionally further comprising at least one additional biologicallyactive compound or agent.

Further noteworthy as embodiments of the present invention arecompositions for controlling an invertebrate pest comprising abiologically effective amount of a compound of any of the precedingEmbodiments, as well as any other embodiments described herein, and anycombinations thereof, and at least one additional component selectedfrom the group consisting of a surfactant, a solid diluent and a liquiddiluent, said compositions optionally further comprising a biologicallyeffective amount of at least one additional biologically active compoundor agent. Embodiments of the invention further include methods forcontrolling an invertebrate pest comprising contacting the invertebratepest or its environment with a biologically effective amount of acompound of any of the preceding Embodiments (e.g., as a compositiondescribed herein).

Embodiments of the invention also include a composition comprising acompound of any of the preceding Embodiments, in the form of a soildrench liquid formulation. Embodiments of the invention further includemethods for controlling an invertebrate pest comprising contacting thesoil with a liquid composition as a soil drench comprising abiologically effective amount of a compound of any of the precedingEmbodiments.

Embodiments of the invention also include a spray composition forcontrolling an invertebrate pest comprising a biologically effectiveamount of a compound of any of the preceding Embodiments and apropellant. Embodiments of the invention further include a baitcomposition for controlling an invertebrate pest comprising abiologically effective amount of a compound of any of the precedingEmbodiments, one or more food materials, optionally an attractant, andoptionally a humectant. Embodiments of the invention also include adevice for controlling an invertebrate pest comprising said baitcomposition and a housing adapted to receive said bait composition,wherein the housing has at least one opening sized to permit theinvertebrate pest to pass through the opening so the invertebrate pestcan gain access to said bait composition from a location outside thehousing, and wherein the housing is further adapted to be placed in ornear a locus of potential or known activity for the invertebrate pest.

One or more of the following methods and variations as described inSchemes 1-12 can be used to prepare the compounds of Formula 1. Thedefinitions of R¹, R², R⁴, R⁵, A¹, A², A³, A⁴, A⁵, A⁶, B¹, B², B³, n andW in the compounds of Formulae 1-15 below are as defined above in theSummary of the Invention unless indicated otherwise. Compounds ofFormulae 1a and 1b are subsets of the compounds of Formula 1, compoundsof Formulae 12a-12c are subsets of the compounds of Formula 12, and thecompound of Formula 15a is a compound of Formula 15.

Compounds of Formula 1a (Formula 1 wherein W is O) can be prepared byaminocarbonylation of aryl bromides or iodides of Formula 2 wherein X isBr or I, with appropriately substituted amino compounds of Formula 3 asshown in Scheme 1.

This reaction is typically carried out with an aryl bromide of Formula 2wherein X is Br in the presence of a palladium catalyst under COatmosphere. The palladium catalysts used for the present methodtypically comprises palladium in a formal oxidation state of either 0(i.e. Pd(0)) or 2 (i.e. Pd(II)). A wide variety of suchpalladium-containing compounds and complexes are useful as catalysts forthe present method. Examples of palladium-containing compounds andcomplexes useful as catalysts in the method of Scheme 1 includePdCl₂(PPh₃)₂ (bis(triphenylphosphine)palladium (II)dichloride),Pd(PPh₃)₄ (tetrakis(triphenylphosphine)palladium(0)), Pd(C₅H₇O₂)₂(palladium(II) acetyl-acetonate), Pd₂(dba)₃(tris(dibenzylideneacetone)dipalladium(0)), and[1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II). The methodof Scheme 1 is generally conducted in a liquid phase, and therefore tobe most effective the palladium catalyst preferably has good solubilityin the liquid phase. Useful solvents include, for example, ethers suchas 1,2-dimethoxyethane, amides such as N,N-dimethylacetamide, andnon-halogenated aromatic hydrocarbons such as toluene.

The method of Scheme 1 can be conducted over a wide range oftemperatures, ranging from about 25 to about 150° C. Of note aretemperatures from about 60 and about 110° C., which typically providefast reaction rates and high product yields. The general methods andprocedures for aminocarbonylation with an aryl bromide and an amine arewell known in the literature; see, for example, H. Horino et al.,Synthesis 1989, 715; and J. J. Li, G. W. Gribble, editors, Palladium inHeterocyclic Chemistry: A Guide for the Synthetic Chemist, 2000. Themethod of Scheme 1 is illustrated in Step C of Example 2 and Step E ofExample 4.

As shown in Scheme 2, compounds of Formula 1b (Formula 1 wherein W is S)can be prepared by treatment of corresponding amide compounds of Formula1a with a thio transfer reagent, such as P₂S₅ (see for example, E.Klingsberg et al., J. Am. Chem. Soc. 1951, 72, 4988; E. C. Taylor Jr. etal., J. Am. Chem. Soc. 1953, 75, 1904; R. Crossley et al., J. Chem. Soc.Perkin Trans. 1 1976, 977) or Lawesson's reagent(2,5-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide;see, for example, S. Prabhakar et al. Synthesis, 1984, 829).

The method of Scheme 2 can be conducted over a wide range oftemperatures, including from about 50 to about 150° C. Of note aretemperatures from about 70 and about 120° C., which typically providefast reaction rates and high product yields. The method of Scheme 2 isillustrated in Example 3.

Compounds of Formula 1a can also be prepared by coupling carboxylicacids of Formula 4 with appropriately substituted amino compounds ofFormula 3 as shown in Scheme 3.

This reaction is generally carried out in the presence of a dehydratingcoupling reagent such as dicyclohexyl carbodiimide,1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-propanephosphonic acidcyclic anhydride or carbonyl diimidazole in the presence of a base suchas triethylamine, pyridine, 4-(dimethylamino)pyridine orN,N-diisopropylethylamine in an anhydrous aprotic solvent such asdichloromethane or tetrahydrofuran at a temperature typically betweenroom temperature and 70° C. The method of Scheme 3 is illustrated inStep E of Example 1.

Compounds of Formula 4 can be prepared by hydrolysis of the ester ofFormula 5, wherein R is methyl or ethyl, as shown in Scheme 4.

In this method, the ester compound of Formula 5 is converted to thecorresponding carboxylic acid of Formula 4 by general procedures wellknown in the art. For example, treatment of a methyl or ethyl ester ofFormula 5 with aqueous lithium hydroxide in tetrahydrofuran, followed byacidification yields the corresponding carboxylic acid of Formula 4. Themethod of Scheme 4 is illustrated in Step D of Example 1.

Compounds of Formula 5 can be prepared by the 1,3-dipolar cycloadditionof styrenes of Formula 7 with nitrile oxides derived from oximes ofFormula 6 as shown in Scheme 5.

This reaction typically proceeds through the intermediacy of an in situgenerated hydroxamyl chloride, which is dehydrochlorinated to thenitrile oxide, which then undergoes 1,3-dipolar cycloaddition with thestyrene 7 to afford compounds of Formula 5. In a typical procedure, achlorinating reagent such as sodium hypochlorite, N-chlorosuccinimide,or chloramine-T is combined with the oxime in the presence of thestyrene. Depending on the conditions, amine bases such as pyridine ortriethylamine may be necessary to facilitate the dehydrochlorinationreaction. The reaction can be run in a wide variety of solventsincluding tetrahydrofuran, diethyl ether, methylene chloride, dioxane,and toluene with temperatures ranging from room temperature to thereflux temperature of the solvent. General procedures for cycloadditionof nitrile oxides with olefins are well documented in the chemicalliterature; for example, see Lee, Synthesis, 1982, 6, 508-509; Kanemasaet al., Tetrahedron, 2000, 56, 1057-1064; EP 1,538,138-A1, as well asreferences cited within. The method of Scheme 4 is illustrated in Step Cof Example 1.

Compounds of Formula 2 can also be prepared by the 1,3-dipolarcycloaddition of styrenes of Formula 7 with nitrile oxides derived fromoximes of Formula 8 as shown in Scheme 6.

In the method of Scheme 6, the compounds of Formula 2 wherein X is ahalogen atom are generated by contacting the compound of Formula 8 witha chlorinating reagent followed by adding a compound of Formula 7. Themethod of Scheme 6 is conducted analogously to the method of Scheme 5already described. The method of Scheme 6 is illustrated in Step B ofExample 2, Step D of Example 4 and Step C of Example 5.

An especially useful group of styrenes for the synthesis of compounds ofFormula 1 are represented by Formula 7a as shown in Scheme 7. Theseintermediates can be prepared by the palladium-catalyzed coupling of anaryl boronic acids of Formula 9 with the commercially available2-bromo-3,3,3-trifluoropropene (Formula 10). General procedures for thisreaction are documented in the chemical literature; see Pan et al., J.Fluorine Chemistry, 1999, 95, 167-170. The method of Scheme 7 isillustrated in Step B of Example 1.

The oximes of Formula 6 can be prepared by the reaction of aldehydes 11with hydroxylamine as shown in Scheme 8. For example, see, H. K. Jung etal. Bioorg. Med. Chem. 2004, 12, 3965.

The aldehydes of Formula 11 can be prepared by a wide variety of methodsknown in the art; some of the aldehydes are known compounds orcommercially available. For example, preparation of the compound ofFormula 11 wherein A¹, A² and A³, A⁴, A³, A², A³, A⁴, A⁵ are CH and R⁹is Me, is disclosed by P. Madenson et al. J. Med. Chem. 2002, 45, 5755.The method of Scheme 8 is illustrated in Step A of Example 1.

As shown in Scheme 9, the oximes of Formula 8, wherein X is a halogenatom, can be prepared from the corresponding aldehydes of Formula 12analogous to the method of Scheme 8. The method of Scheme 9 isillustrated in Step A of Example 2, Step C of Example 4 and Step B ofExample 5.

Compounds of Formula 12 are commercially available or known compounds,or they can be prepared by a wide variety of methods known in the art.For example, a compound of Formula 12 can be prepared by directfomylation of the corresponding aryl halides, see G. E. Boswell et al.J. Org. Chem. 1995, 65, 6592; or by reduction of the corresponding arylesters, see references P. R. Bernstein et al. Bioorg. Med. Chem. Lett.2001, 2769 and L. W. Deady et al. Aust. J. Chem. 1989, 42, 1029. For aspecific example, as shown in Scheme 10, aldehydes of Formula 12 can beprepared from the corresponding methyl-substituted compounds of Formula13 (wherein X is halogen) by reacting with N-bromosuccinimide (NBS) inthe presence of 2,2′-azobis(2-methylpropionitrile) (AIBN) and sodiumacetate to give acetates of Formula 14, which are then converted to thealdehydes of Formula 12 by esterification and oxidation. The method ofScheme 10 is illustrated in Example 4, Steps A and B.

The compounds of Formula 13 are commercially available or knowncompounds, or they can be prepared by a wide variety of methods known inthe art. For example, a compound of Formula 13, wherein A³ is N, A¹, A²,A⁴, A⁵ and A⁶ are CH, can be prepared as disclosed in Molecules, 2004,9, 178.

An alternative method for preparing aldehydes of Formula 12 (wherein Xis a halogen atom) is shown in Scheme 11. The formyl group of Formula 12can be introduced to the 10-membered aromatic ring system by displacingthe bromo substituent of a compound of Formula 15. For references ofthis general method, see Synthesis, 2006, 293 and Bioorg. Med. Chem.2004, 12, 715. The method of Scheme 11 is illustrated in Step A ofExample 5.

As shown in Scheme 12, aldehydes of Formulae 12b and 12c can be preparedfrom 5,8-dibromoisoquinoline (Formula 15a) by treating the compound ofFormula 15a with n-BuLi at −78° C. and quenching withN,N-dimethylformamide.

The compound of Formula 15a can be prepared by the method disclosed inSynthesis, 2002, 83; see, for example, or by the method of G. E. Boswellet al. J. Org. Chem. 1995, 65, 6592. Alternatively, aryl aldehydes ofFormula 12 can be prepared by a wide variety of other methods known inthe art, e.g., by reduction of the corresponding aryl esters, seereferences P. R. Bernstein et al. Bioorg. Med. Chem. Lett. 2001, 2769and L. W. Deady et al. Aust. J. Chem. 1989, 42, 1029.

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “t” meanstriplet, “m” means multiplet, “dd” means doublet of doublets, and “br s”means broad singlet.

Example 1 Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamideStep A: Preparation of methyl4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate

To a stirred solution of methyl 4-formyl-1-naphthalenecarboxylate (2.2g, 10.3 mmol) in methanol (50 mL) was added a solution of hydroxylamine(1.33 mL, 50% in water). After stirring at room temperature for 2 h, thereaction mixture was concentrated under reduced pressure to provide thetitle compound as a pale yellow solid (2.55 g).

¹H NMR (CDCl₃): 8.93 (d, 1H), 8.86 (s, 1H), 8.41 (d, 1H), 8.14 (d, 1H),7.82 (d, 1H), 7.63 (m, 2H), 4.02 (s, 3H).

Step B: Preparation of1,3-dichloro-5-[1-(trimethylfluoromethyl)ethenyl]benzene

To a mixture of tetrahydrofuran (33 mL), 1,2-dimethoxyethane (33 mL),and 4 N aqueous potassium hydroxide (33 mL) in a 200 mL Fisher-Portersealed tube was added 3,5-dichlorophenylboronic acid (8.72 g, 45.7 mmol)and 2-bromo-3,3,3-trifluoropropene (10.0 g, 57.2 mmol), followed by theaddition of tetrakis(triphenylphosphine)palladium (0) (264 mg, 0.229mmol). Then the mixture was heated to 75° C. for 3 h. The reactionmixture was partitioned between diethyl ether and water. The aqueousextract was washed with diethyl ether (2×20 mL). The organic extractswere combined, dried (MgSO₄), and concentrated under reduced pressure.The residue was purified by silica gel chromatography usinghexanes/ethyl acetate as eluent to afford the title compound as a clearoil (4.421 g).

¹H NMR (CDCl₃): δ 7.41 (s, 2H), 7.33 (s, 1H), 6.04 (d, 1H), 5.82 (d,1H).

Step C: Preparation of methyl4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

To a stirred solution of methyl4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate (i.e. the product fromStep A) (1.0 g, 4.36 mmol) in N,N-dimethylformamide (5.0 mL) was addedN-chlorosuccinimide (1.16 g, 8.72 mmol). This mixture was stirred for1.5 h at room temperature, and then a solution of1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the productfrom Step B) (3.20 g, 13.1 mmol) and triethylamine (6.1 mL, 43.6 mmol)in N,N-dimethylformamide (4.0 mL) was added. After stiffing foradditional 2 h at room temperature, the reaction mixture was dilutedwith water and extracted with ethyl acetate. The organic layer waswashed with brine, dried (Na₂SO₄), and concentrated under reducedpressure. The residue was purified by silica gel chromatography usinghexanes/ethyl acetate as eluent to afford the title compound as a paleyellow oil (700 mg, 34% yield).

¹H NMR (CDCl₃): 8.88 (d, 1H), 8.80 (d, 1H), 8.10 (d, 1H), 7.68 (m, 2H),7.55 (m, 3H), 7.46 (dd, 1H), 4.27 (d, 1H), 4.03 (s, 3H), 3.91 (d, 1H).

Step D: Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylicacid

To a stirred solution of methyl4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate(i.e. the product from Step C) (650 mg, 1.39 mmol) in tetrahydrofuran(10 mL) was added a solution of lithium hydroxide monohydrate (350 mg,8.34 mmol) in water (10 mL), followed by methanol (10 mL). The resultingmixture was stirred overnight at room temperature. The reaction mixturewas partitioned between water and diethyl ether. Then the aqueous layerwas acidified with 6 N aqueous hydrochloric acid to pH 2 and extractedwith ethyl acetate. The combined organic layers were washed with brine,dried and concentrated to provide the title compound as a white solid(450 mg).

¹H NMR (CDCl₃): 9.08 (d, 1H), 8.80 (d, 1H), 8.31 (d, 1H), 7.71 (m, 2H),7.57 (m, 3H), 7.46 (dd, 1H), 4.28 (d, 1H), 3.91 (d, 1H).

Step E: Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide

A mixture of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylicacid (i.e. the product from Step C) (190 mg, 0.42 mmol),4-(dimethylamino)pyridine (77 mg, 0.63 mmol), propylphosphonic anhydride(0.38 mL, 0.63 mmol, 50% in ethyl acetate) and 2,2,2-trifluoroethylamine(0.033 mL, 0.42 mL) in dichloromethane (5 mL) was stirred at roomtemperature overnight. The reaction mixture was concentrated, and theresidue was purified by column chromatography on silica gel usinghexanes/ethyl acetate as eluent to give the title product, a compound ofthe present invention, as a white solid (71 mg).

¹H NMR (CDCl₃): 8.78 (d, 1H), 8.18 (d, 1H), 7.63 (m, 2H), 7.56 (m, 2H),7.52 (d, 1H), 7.46 (m, 1H), 7.44 (d, 1H), 6.41 (t, 1H), 4.23 (d, 1H),4.20 (m, 2H), 3.87 (d, 1H).

Example 2 Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamideStep A: Preparation of 4-bromo-1-naphthalenecarboxylate oxime

To a stirred solution of 4-bromo-1-naphthalenecarboxaldehyde (3.7 g,15.7 mmol) in ethanol (30 mL) was added an aqueous solution ofhydroxylamine (1.25 mL, 50% in water). After stirring at roomtemperature for 3 h, the reaction mixture was concentrated under reducedpressure to provide the title compound as a pale yellow solid (3.8 g).

¹H NMR (DMSO-d₆): 11.60 (s, 1H), 8.81 (s, 1H), 8.71 (d, 1H), 8.24 (d,1H), 7.95 (d, 1H), 7.74 (m, 3H).

Step B: Preparation of3-(4-bromo-1-naphthalenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole

To a stirred solution of 4-bromo-1-naphthalenecarboxylate oxime (i.e.the product from Step A) (2.33 g, 9.3 mmol) in N,N-dimethylformamide(6.0 mL) was added N-chlorosuccinimide (1.70 g, 12.7 mmol). The reactionmixture was stirred for 1 h at room temperature, and then a solution of1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the productfrom Step B of Example 1) (2.70 g, 11.2 mmol) and triethylamine (4.5 mL,32.0 mmol) in N,N-dimethylformamide (9.0 mL) was added. After stiffingfor additional 2 h at room temperature, the reaction mixture was dilutedwith water and extracted with ethyl acetate. The organic layer waswashed with brine, dried (Na₂SO₄), and concentrated under reducedpressure. The residue was purified by silica gel column chromatographyusing hexanes/ethyl acetate as eluent to afford the title compound as awhite solid (2.9 g, 64% yield).

¹H NMR (CDCl₃): 8.87 (m, 1H), 8.32 (m, 1H), 7.77 (d, 1H), 7.66 (m, 2H),7.55 (s, 2H), 7.46 (dd, 1H), 7.32 (d, 1H), 4.24 (d, 1H), 3.88 (d, 3H).

Step C: Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamide

A mixture of3-(4-bromo-1-naphthalenyl)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole(i.e. the product from Step B) (1.0 g, 2.04 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(PdCl₂(dppf)) (0.22 g, 0.30 mmol), 2-(aminomethyl)pyridine (0.86 g, 7.96mmol) and triethylamine (5.6 mL, 40 mmol) in toluene (15 mL) was purgedwith carbon monoxide for 15 minutes. Then the reaction vial wasmaintained with carbon monoxide using a balloon. The reaction mixturewas stirred at 70° C. under carbon monoxide atmosphere overnight. Themixture was cooled to room temperature, filtered through a short pad ofCelite® diatomaceous filter aid and rinsed with small amount of ethylacetate. The filtrate was concentrated, and the residue was purified bycolumn chromatography on silica gel using hexanes/ethyl acetate aseluent to provide the title product, a compound of the presentinvention, as a white solid (0.72 g, 65% yield).

¹H NMR (CDCl₃): 8.81 (d, 1H), 8.55 (d, 1H), 8.38 (d, 1H), 7.80-7.27 (m,10H), 4.89 (d, 2H), 4.22 (d, 1H), 3.86 (d, 1H).

Example 3 Preparation of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarbothioamide

A mixture of4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamide(i.e. the product from Example 2) (40 mg, 0.073 mmol) and2,5-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide(Lawesson's reagent) (18 mg, 0.044 mmol) in toluene (2 mL) was heated atreflux for 2 h. The reaction mixture was cooled to room temperature, anddirectly purified by silica gel column chromatography usinghexanes/ethyl acetate as eluent to provide the title product, a compoundof the present invention, as a yellow solid (29 mg, 71% yield).

¹H NMR (CDCl₃): 9.41 (br s 1H), 8.91 (dd, 1H), 8.70 (dd, 1H), 8.46 (d,1H), 8.21 (d, 1H), 7.75 (dt, 1H), 7.64 (d, 1H), 7.57 (s, 2H), 7.47 (dd,1H), 7.43 (t, 1H), 7.38 (d, 1H), 7.24 (dd, 1H), 5.14 (d, 2H), 4.68 (d,1H), 4.39 (d, 1H).

Example 4 Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-quinolinecarboxamideStep A: Preparation of (8-bromo-5-quinolinyl)methyl acetate

A mixture of 8-bromo-5-methylquinoline (5.4 g, 24.3 mmol),N-bromosuccinimide (5.2 g, 29.2 mmol), and2,2′-azobis(2-methylpropionitrile) (AIBN) (0.40 g, 24.3 mmol) in carbontetrachloride (80 mL) was heated at reflux for 3 h under nitrogenatmosphere. The reaction mixture was cooled to room temperature andfiltered, using hexane for rinsing. The filtrate was concentrated underreduced pressure. The residue was dissolved in N,N-dimethylformamide (50mL), and then sodium acetate (4.0 g, 48.8 mmol) was added. The resultingmixture was stirred at 100° C. for 2 h under nitrogen atmosphere. Thereaction mixture was cooled to room temperature, diluted with water andextracted with a mixture of ethyl acetate and hexane (3:7). The organiclayer was washed with brine, dried (Na₂SO₄), and concentrated underreduced pressure. The crude product was purified by columnchromatography on silica gel using hexanes/ethyl acetate as eluent toafford the title product as a pale yellow solid (4.8 g).

Step B: Preparation of 8-bromo-5-quinolinecarboxaldehyde

A mixture of the (8-bromo-5-quinolinyl)methyl acetate (i.e. the productfrom Step A) and methanol (50 mL) was heated at reflux for 1 h in thepresence of trace amount of potassium carbonate (10 mg). Then thereaction mixture was cooled to room temperature and concentrated underreduced pressure to provide the corresponding alcohol in quantitativeyield as a pale yellow solid.

To a stirred solution of the crude alcohol (2.0 g, 8.3 mmol) indichloromethane (60 mL) was added slowly1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martinperiodinane) (4.0 g, 9.4 mmol) at room temperature. After stirring for0.5 h, the reaction mixture was diluted with dichloromethane, washedwith saturated aqueous sodium bicarbonate and brine, dried (Na₂SO₄), andconcentrated under reduced pressure. The crude product was purified bycolumn chromatography on silica gel using hexanes/ethyl acetate aseluent to afford the title product as a white solid (1.8 g).

¹H NMR (CDCl₃): 10.31 (s, 1H), 9.65 (dd, 1H), 9.12 (dd, 1H), 8.26 (d,1H), 7.88 (d, 1H), 7.66 (dd, 1H).

Step C: Preparation of 8-bromo-5-quinolinecarboxaldehyde oxime

To a stirred solution of 8-bromo-5-quinolinecarboxaldehyde (i.e. theproduct from Step B) (1.7 g, 7.1 mmol) in ethanol (30 mL) was added anaqueous solution of hydroxylamine (0.7 mL, 50% in water). After stirringat room temperature for 2 h, the reaction mixture was concentrated underreduced pressure to provide the title compound as a pale yellow solid(1.8 g).

¹H NMR (DMSO-d₆): 11.61 (s, 1H), 9.16 (dd, 1H), 9.07 (dd, 1H), 8.79 (s,1H), 8.20 (d, 1H), 7.79 (d, 1H), 7.72 (dd, 1H).

Step D: Preparation of8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]quinoline

To a stirred solution of 8-bromo-5-quinolinecarboxaldehyde oxime (i.e.the product from Step C) (1.7 g, 6.8 mmol) in N,N-dimethylformamide(13.0 mL) was added N-chlorosuccinimide (1.24 g, 9.3 mmol). The reactionmixture was stirred for 1 h at room temperature, and then a solution of1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (i.e. the productfrom Example 1, Step B) (1.96 g, 8.1 mmol) and triethylamine (2.86 mL,20.4 mmol) in N,N-dimethylformamide (7.0 mL) was added. After stirringfor additional 12 h at room temperature, the reaction mixture wasdiluted with water and extracted with ethyl acetate. The organic layerwas washed with brine, dried (Na₂SO₄), and concentrated under reducedpressure. The residue was purified by column chromatography on silicagel using hexanes/ethyl acetate as eluent to afford the title compoundas a white solid (2.0 g, 61% yield).

¹H NMR (CDCl₃): 9.39 (dd, 1H), 9.08 (dd, 1H), 8.05 (d, 1H), 7.59 (dd,1H), 7.55 (s, 2H), 7.44 (t, 1H), 7.40 (d, 1H), 4.27 (d, 1H), 3.92 (d,1H).

Step E: Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-quinolinecarboxamide

A mixture of8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]quinoline(i.e. the product from Step D) (500 mg, 1.0 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(PdCl₂(dppf)) (75 mg, 0.10 mmol), 2-(aminomethyl)pyridine (0.43 mL, 4.0mmol) and triethylamine (2.8 mL, 20 mmol) in toluene (10 mL) was purgedwith carbon monoxide for 15 minutes. Then the reaction vial wasmaintained with carbon monoxide using a balloon. The reaction mixturewas stirred at 70° C. under carbon monoxide atmosphere overnight. Themixture was cooled to room temperature, filtered through a short pad ofCelite® diatomaceous filter aid and rinsed with small amount of ethylacetate. The filtrate was concentrated, and the residue was purified bycolumn chromatography on silica gel using hexanes/ethyl acetate aseluent to provide the title product, a compound of the presentinvention, as a brown foamy solid (60 mg, 11% yield).

¹H NMR (CDCl₃): 12.02 (br s 1H), 9.52 (d, 1H), 9.01 (s, 1H), 8.88 (d,1H), 8.62 (d, 1H), 7.60-7.74 (m, 3H), 7.56 (s, 2H), 7.45 (br s 2H), 7.20(dd, 1H), 4.96 (d, 2H), 4.32 (d, 1H), 3.98 (d, 1H).

Example 5 Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-isoquinolinecarboxamideStep A: Preparation of 8-bromo-5-isoquinolinecarboxaldehyde and5-bromo-8-isoquinolinecarboxaldehyde

To a stirred mixture of 5,8-dibromoisoquinoline (4.0 g. 13.9 mmol) intetrahydrofuran (120 mL) at −78° C. under nitrogen atmosphere was addeddropwise a solution of n-butyllithium (2.3 M in hexane, 7.3 mL, 16.8mmol). The reaction mixture turned dark. After stirring for 15 minutes,the reaction mixture was quenched by adding N,N-dimethylformamide (4.0mL). After stirring at −78° C. for an additional 1 h, the reactionmixture was quenched with water, extracted with mixture of ethylacetate/hexane (2:8), washed with water and brine, dried (Na₂SO₄), andconcentrated under reduced pressure. The residue was purified by columnchromatography on silica gel using hexanes/ethyl acetate as eluent toafford the 8-bromo-5-isoquinolinecarboxaldehyde (0.10 g), followed by5-bromo-8-isoquinolinecarboxaldehyde (1.0 g) as white solids.

¹H NMR (CDCl₃) of 8-bromo-5-isoquinolinecarboxaldehyde: 10.36 (s, 1H),9.72 (s, 1H), 9.00 (d, 1H), 8.79 (d, 1H), 8.04 (d, 1H), 8.01 (dd, 1H);and

¹H NMR (CDCl₃) of 5-bromo-8-isoquinolinecarboxaldehyde: 10.57 (s, 1H),10.41 (s, 1H), 8.81 (d, 1H), 8.18 (d, 1H), 8.11 (d, 1H), 7.94 (d, 1H).

Step B: Preparation of 8-bromo-5-isoquinolinecarboxaldehyde oxime

To a stirred solution of 8-bromo-5-isoquinolinecarboxaldehyde (i.e. aproduct from Step A) (75 mg, 0.3 mmol) in ethanol (7 mL) was added anaqueous solution of hydroxylamine (0.5 mL, 50% in water). After stirringat room temperature overnight, the reaction mixture was concentratedunder reduced pressure to provide the title compound as a yellow solid(70 mg).

¹H NMR (DMSO-d₆): 11.75 (s, 1H), 9.55 (s, 1H), 8.78 (s, 1H), 8.71 (d,1H), 8.59 (d, 1H), 8.07 (d, 1H), 7.96 (d, 1H).

Step C: Preparation of8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]isoquinoline

To a stirred solution of 8-bromo-5-isoquinolinecarboxaldehyde oxime(i.e. the product from Step B) (70 mg, 0.28 mmol) inN,N-dimethylformamide (2.0 mL) was added N-chlorosuccinimide (64 g, 0.48mmol). The reaction mixture was stirred for 0.5 h at room temperature,and then a solution of1,3-dichloro-5-[1-(trifluoromethyl)ethenyl]benzene (135 mg, 0.56 mmol)(i.e. the product from Example 1, Step B) and triethylamine (0.12 mL,0.86 mmol) in N,N-dimethylformamide (1.5 mL) was added. After stirringfor an additional 12 h at room temperature, the reaction mixture wasdiluted with water and extracted with ethyl acetate. The organic layerwas washed with brine, dried (Na₂SO₄), and concentrated under reducedpressure. The residue was purified by silica gel column chromatographyusing hexanes/ethyl acetate as eluent to afford the title compound (20mg) contaminated with some impurity.

Step D: Preparation of5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-isoquinolinecarboxamide

A mixture of8-bromo-5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]isoquinoline(i.e. the product from Step C) (20 mg, 0.04 mmol),[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(PdCl₂(dppf)) (6 mg, 0.008 mmol), 2-(aminomethyl)pyridine (17 mg, 0.16mmol) and triethylamine (0.1 mL, 0.7 mmol) in toluene (2 mL) was purgedwith carbon monoxide for 15 minutes. Then the reaction vial wasmaintained with carbon monoxide using a balloon. The reaction mixturewas stirred at 70° C. under carbon monoxide atmosphere overnight. Themixture was cooled to room temperature, filtered through a short pad ofCelite® diatomaceous filter and rinsed with small amount of ethylacetate. The filtrate was concentrated and the residue was purified bycolumn chromatography on silica gel using hexanes/ethyl acetate aseluent to provide the title product, a compound of the presentinvention, as a pale white solid (15 mg).

¹H NMR (CDCl₃): 9.77 (s, 1H), 8.80 (d, 1H), 8.70 (d, 1H), 8.52 (s, 1H),7.81-7.23 (m, 9H), 4.88 (d, 2H), 4.28 (d, 1H), 3.92 (d, 1H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 9 can be prepared. Thefollowing abbreviations are used in the Tables which follow: —CN meanscyano, Ph means phenyl, Py means pyridinyl, Me means methyl, Et meansethyl and i-Pr means isopropyl.

TABLE 1

  wherein m is 1, 2, 3, 4 or 5. R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H H CH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl,4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃ CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H HCH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H HCH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃ 4-I H H CH₂CF₃ CF₃ 3-CN H HCH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF₃ HH CH₂CF₃ CF₃ H Cl H CH₂CF₃ CF₃ 2-Cl Cl H CH₂CF₃ CF₃ 3-Cl Cl H CH₂CF₃ CF₃4-Cl Cl H CH₂CF₃ CF₃ 2-Cl, 4-Cl Cl H CH₂CF₃ CF₃ 3-Cl, 4-Cl Cl H CH₂CF₃CF₃ 3-Cl, 5-Cl Cl H CH₂CF₃ CF₃ 2-F Cl H CH₂CF₃ CF₃ 3-F Cl H CH₂CF₃ CF₃4-F Cl H CH₂CF₃ CF₃ 2-F, 4-F Cl H CH₂CF₃ CF₃ 3-F, 4-F Cl H CH₂CF₃ CF₃3-F, 5-F Cl H CH₂CF₃ CF₃ 3-CF₃ Cl H CH₂CF₃ CF₃ 4-CF₃ Cl H CH₂CF₃ CF₃3-CF₃, 5-CF₃ Cl H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Cl H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ ClH CH₂CF₃ CF₃ 3-Cl, 4-Br Cl H CH₂CF₃ CF₃ 3-Br, 5-Br Cl H CH₂CF₃ CF₃ 3-Br,4-Br Cl H CH₂CF₃ CF₃ 3-Br Cl H CH₂CF₃ CF₃ 4-Br Cl H CH₂CF₃ CF₃ 3-I Cl HCH₂CF₃ CF₃ 4-I Cl H CH₂CF₃ CF₃ 3-CN Cl H CH₂CF₃ CF₃ 4-CN Cl H CH₂CF₃ CF₃3-Me Cl H CH₂CF₃ CF₃ 4-Me Cl H CH₂CF₃ CF₃ 3-OMe Cl H CH₂CF₃ CF₃ 4-OMe ClH CH₂CF₃ CF₃ 3-OCF₃ Cl H CH₂CF₃ CF₃ 4-OCF₃ Cl H CH₂CF₃ CF₃ H Me HCH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 4-Cl Me HCH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H CH₂-2-Py CF₃3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 4-CF₃ Me HCH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₃ 3-Br,5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₃ 3-Br Me H CH₂-2-PyCF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 4-I Me H CH₂-2-Py CF₃3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-Me Me H CH₂-2-Py CF₃4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMe Me H CH₂-2-Py CF₃3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF₃ Me H CH₂-2-Py CF₂CF₃ H H H CH₂CF₃ CF₂CF₃2-Cl H H CH₂CF₃ CF₂CF₃ 3-Cl H H CH₂CF₃ CF₂CF₃ 4-Cl H H CH₂CF₃ CF₂CF₃2-Cl, 4-Cl H H CH₂CF₃ CF₂CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₂CF₃ 3-Cl, 5-Cl H HCH₂CF₃ CF₂CF₃ 2-F H H CH₂CF₃ CF₂CF₃ 3-F H H CH₂CF₃ CF₂CF₃ 4-F H H CH₂CF₃CF₂CF₃ 2-F, 4-F H H CH₂CF₃ CF₂CF₃ 3-F, 4-F H H CH₂CF₃ CF₂CF₃ 3-F, 5-F HH CH₂CF₃ CF₂CF₃ 3-CF₃ H H CH₂CF₃ CF₂CF₃ 4-CF₃ H H CH₂CF₃ CF₂CF₃ 3-CF₃,5-CF₃ H H CH₂CF₃ CF₂CF₃ 3-Cl, 5-CF₃ H H CH₂CF₃ CF₂CF₃ 3-Cl, 4-CF₃ H HCH₂CF₃ CF₂CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₂CF₃ 3-Br, 5-Br H H CH₂CF₃ CF₂CF₃3-Br, 4-Br H H CH₂CF₃ CF₂CF₃ 3-Br H H CH₂CF₃ CF₂CF₃ 4-Br H H CH₂CF₃CF₂CF₃ 3-I H H CH₂CF₃ CF₂CF₃ 4-I H H CH₂CF₃ CF₂CF₃ 3-CN H H CH₂CF₃CF₂CF₃ 4-CN H H CH₂CF₃ CF₂CF₃ 3-Me H H CH₂CF₃ CF₂CF₃ 4-Me H H CH₂CF₃CF₂CF₃ 3-OMe H H CH₂CF₃ CF₂CF₃ 4-OMe H H CH₂CF₃ CF₂CF₃ 3-OCF₃ H H CH₂CF₃CF₂CF₃ 4-OCF₃ H H CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃CF(CF₃)₂ 3-Cl H H CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl HH CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CF₃CF(CF₃)₂ 2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂ 4-F H H CH₂CF₃CF(CF₃)₂ 2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F,5-F H H CH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 4-CF₃ H H CH₂CF₃CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃ CF(CF₃)₂3-Br, 5-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br H HCH₂CF₃ CF(CF₃)₂ 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 4-I H HCH₂CF₃ CF(CF₃)₂ 3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H H CH₂CF₃ CF(CF₃)₂ 3-Me HH CH₂CF₃ CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂4-OMe H H CH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ H H CH₂CF₃CF₃ H Me H CH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me H CH₂CF₃ CF₃ 4-Cl MeH CH₂CF₃ CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl,5-Cl Me H CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me H CH₂CF₃ CF₃ 4-F Me HCH₂CF₃ CF₃ 2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 5-F MeH CH₂CF₃ CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ MeH CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃3-Cl, 4-Br Me H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃ 3-Br, 4-Br Me HCH₂CF₃ CF₃ 3-Br Me H CH₂CF₃ CF₃ 4-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃4-I Me H CH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 4-CN Me H CH₂CF₃ CF₃ 3-Me Me HCH₂CF₃ CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃CF₃ 3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF₃ Me H CH₂CF₃ CF₃ H H H CH₂-2-Py CF₃2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 4-Cl H H CH₂-2-Py CF₃ 2-Cl,4-Cl H H CH₂-2-Py CF₃ 3-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 5-Cl H HCH₂-2-Py CF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃ 4-F H H CH₂-2-PyCF₃ 2-F, 4-F H H CH₂-2-Py CF₃ 3-F, 4-F H H CH₂-2-Py CF₃ 3-F, 5-F H HCH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-Py CF₃ 4-CF₃ H H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ H H CH₂-2-PyCF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃ 3-Br, 4-Br HH CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃ 3-I H HCH₂-2-Py CF₃ 4-I H H CH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H HCH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 4-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF₃ H HCH₂-2-Py CF₃ H Cl H CH₂-2-Py CF₃ 2-Cl Cl H CH₂-2-Py CF₃ 3-Cl Cl HCH₂-2-Py CF₃ 4-Cl Cl H CH₂-2-Py CF₃ 2-Cl, 4-Cl Cl H CH₂-2-Py CF₃ 3-Cl,4-Cl Cl H CH₂-2-Py CF₃ 3-Cl, 5-Cl Cl H CH₂-2-Py CF₃ 2-F Cl H CH₂-2-PyCF₃ 3-F Cl H CH₂-2-Py CF₃ 4-F Cl H CH₂-2-Py CF₃ 2-F, 4-F Cl H CH₂-2-PyCF₃ 3-F, 4-F Cl H CH₂-2-Py CF₃ 3-F, 5-F Cl H CH₂-2-Py CF₃ 3-CF₃ Cl HCH₂-2-Py CF₃ 4-CF₃ Cl H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Cl H CH₂-2-Py CF₃3-Cl, 5-CF₃ Cl H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ Cl H CH₂-2-Py CF₃ 3-Cl, 4-BrCl H CH₂-2-Py CF₃ 3-Br, 5-Br Cl H CH₂-2-Py CF₃ 3-Br, 4-Br Cl H CH₂-2-PyCF₃ 3-Br Cl H CH₂-2-Py CF₃ 4-Br Cl H CH₂-2-Py CF₃ 3-I Cl H CH₂-2-Py CF₃4-I Cl H CH₂-2-Py CF₃ 3-CN Cl H CH₂-2-Py CF₃ 4-CN Cl H CH₂-2-Py CF₃ 3-MeCl H CH₂-2-Py CF₃ 4-Me Cl H CH₂-2-Py CF₃ 3-OMe Cl H CH₂-2-Py CF₃ 4-OMeCl H CH₂-2-Py CF₃ 3-OCF₃ Cl H CH₂-2-Py CF₃ 4-OCF₃ Cl H CH₂-2-Py CF₂CF₃ HMe H CH₂-2-Py CF₂CF₃ 2-Cl Me H CH₂-2-Py CF₂CF₃ 3-Cl Me H CH₂-2-Py CF₂CF₃4-Cl Me H CH₂-2-Py CF₂CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₂CF₃ 3-Cl, 4-Cl MeH CH₂-2-Py CF₂CF₃ 3-Cl, 5-Cl Me H CH₂-2-Py CF₂CF₃ 2-F Me H CH₂-2-PyCF₂CF₃ 3-F Me H CH₂-2-Py CF₂CF₃ 4-F Me H CH₂-2-Py CF₂CF₃ 2-F, 4-F Me HCH₂-2-Py CF₂CF₃ 3-F, 4-F Me H CH₂-2-Py CF₂CF₃ 3-F, 5-F Me H CH₂-2-PyCF₂CF₃ 3-CF₃ Me H CH₂-2-Py CF₂CF₃ 4-CF₃ Me H CH₂-2-Py CF₂CF₃ 3-CF₃,5-CF₃ Me H CH₂-2-Py CF₂CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-Py CF₂CF₃ 3-Cl, 4-CF₃Me H CH₂-2-Py CF₂CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₂CF₃ 3-Br, 5-Br Me HCH₂-2-Py CF₂CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₂CF₃ 3-Br Me H CH₂-2-PyCF₂CF₃ 4-Br Me H CH₂-2-Py CF₂CF₃ 3-I Me H CH₂-2-Py CF₂CF₃ 4-I Me HCH₂-2-Py CF₂CF₃ 3-CN Me H CH₂-2-Py CF₂CF₃ 4-CN Me H CH₂-2-Py CF₂CF₃ 3-MeMe H CH₂-2-Py CF₂CF₃ 4-Me Me H CH₂-2-Py CF₂CF₃ 3-OMe Me H CH₂-2-PyCF₂CF₃ 4-OMe Me H CH₂-2-Py CF₂CF₃ 3-OCF₃ Me H CH₂-2-Py CF₂CF₃ 4-OCF₃ MeH CH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-Py CF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂3-Cl Me H CH₂-2-Py CF(CF₃)₂ 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me HCH₂-2-Py CF(CF₃)₂ 2-F Me H CH₂-2-Py CF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂4-F Me H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me HCH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me H CH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br, 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I Me H CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-PyCF(CF₃)₂ 3-CN Me H CH₂-2-Py CF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me MeH CH₂-2-Py CF(CF₃)₂ 4-Me Me H CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-PyCF(CF₃)₂ 4-OMe Me H CH₂-2-Py CF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂4-OCF₃ Me H CH₂-2-Py

TABLE 2

  wherein m is 1, 2, 3, 4 or 5. R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H H CH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl,4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃ CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H HCH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H HCH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃ 4-I H H CH₂CF₃ CF₃ 3-CN H HCH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF₃ HH CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl HH CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H HCH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 4-CF₃ H H CH₂CF₃ CF(CF₃)₂3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br H HCH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br H H CH₂CF₃ CF(CF₃)₂4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H H CH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂ 4-OMe H HCH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ H H CH₂CF₃ CF₃ H Me HCH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me H CH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 5-Cl MeH CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me H CH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-BrMe H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃3-Br Me H CH₂CF₃ CF₃ 4-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me HCH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl Me H CH₂CF₃ CF(CF₃)₂ 4-Cl Me HCH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F MeH CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me HCH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃ CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CNMe H CH₂CF₃ CF(CF₃)₂ 4-CN Me H CH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂4-Me Me H CH₂CF₃ CF(CF₃)₂ 3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ Me H CH₂CF₃ CF₃ H H HCH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 4-Cl H HCH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃ 3-F, 4-F H H CH₂-2-Py CF₃3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-Py CF₃ 4-CF₃ H H CH₂-2-Py CF₃3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ HH CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H HCH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 4-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF₃ H HCH₂-2-Py CF(CF₃)₂ H H H CH₂-2-Py CF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-Py CF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H HCH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-Py CF(CF₃)₂ 3-CF₃ H H CH₂-2-PyCF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br,4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-Py CF(CF₃)₂ 4-Br H H CH₂-2-PyCF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H H CH₂-2-Py CF(CF₃)₂ 3-CN H HCH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂ 3-Me H H CH₂-2-Py CF(CF₃)₂4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-Py CF(CF₃)₂ 4-OMe H HCH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ H H CH₂-2-Py CF₃ HMe H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 4-Cl MeH CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H CH₂-2-Py CF₃3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 4-CF₃ Me HCH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₃ 3-Br,5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₃ 3-Br Me H CH₂-2-PyCF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 4-I Me H CH₂-2-Py CF₃3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-Me Me H CH₂-2-Py CF₃4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMe Me H CH₂-2-Py CF₃3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-PyCF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-Py CF(CF₃)₂ 4-Cl MeH CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-F Me H CH₂-2-PyCF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-Py CF(CF₃)₂ 2-F, 4-FMe H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I MeH CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me H CH₂-2-PyCF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-Py CF(CF₃)₂ 4-Me MeH CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMe Me H CH₂-2-PyCF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ Me H CH₂-2-Py

TABLE 3

  wherein m is 1, 2, 3, 4 or 5. R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H H CH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl,4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃ CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H HCH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H HCH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃ 4-I H H CH₂CF₃ CF₃ 3-CN H HCH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF₃ HH CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl HH CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H HCH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 4-CF₃ H H CH₂CF₃ CF(CF₃)₂3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br H HCH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br H H CH₂CF₃ CF(CF₃)₂4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H H CH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂ 4-OMe H HCH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ H H CH₂CF₃ CF₃ H Me HCH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me H CH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 5-Cl MeH CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me H CH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-BrMe H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃3-Br Me H CH₂CF₃ CF₃ 4-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me HCH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl Me H CH₂CF₃ CF(CF₃)₂ 4-Cl Me HCH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F MeH CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me HCH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃ CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CNMe H CH₂CF₃ CF(CF₃)₂ 4-CN Me H CH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂4-Me Me H CH₂CF₃ CF(CF₃)₂ 3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ Me H CH₂CF₃ CF₃ H H HCH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 4-Cl H HCH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃ 3-F, 4-F H H CH₂-2-Py CF₃3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-Py CF₃ 4-CF₃ H H CH₂-2-Py CF₃3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ HH CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H HCH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 4-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF₃ H HCH₂-2-Py CF(CF₃)₂ H H H CH₂-2-Py CF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-Py CF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H HCH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-Py CF(CF₃)₂ 3-CF₃ H H CH₂-2-PyCF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br,4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-Py CF(CF₃)₂ 4-Br H H CH₂-2-PyCF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H H CH₂-2-Py CF(CF₃)₂ 3-CN H HCH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂ 3-Me H H CH₂-2-Py CF(CF₃)₂4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-Py CF(CF₃)₂ 4-OMe H HCH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ H H CH₂-2-Py CF₃ HMe H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 4-Cl MeH CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H CH₂-2-Py CF₃3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 4-CF₃ Me HCH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₃ 3-Br,5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₃ 3-Br Me H CH₂-2-PyCF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 4-I Me H CH₂-2-Py CF₃3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-Me Me H CH₂-2-Py CF₃4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMe Me H CH₂-2-Py CF₃3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-PyCF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-Py CF(CF₃)₂ 4-Cl MeH CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-F Me H CH₂-2-PyCF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-Py CF(CF₃)₂ 2-F, 4-FMe H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I MeH CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me H CH₂-2-PyCF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-Py CF(CF₃)₂ 4-Me MeH CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMe Me H CH₂-2-PyCF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ Me H CH₂-2-Py

TABLE 4

  wherein m is 1, 2, 3, 4 or 5. R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H H CH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl,4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃ CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H HCH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H HCH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃ 4-I H H CH₂CF₃ CF₃ 3-CN H HCH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF₃ HH CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl HH CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H HCH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 4-CF₃ H H CH₂CF₃ CF(CF₃)₂3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br H HCH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br H H CH₂CF₃ CF(CF₃)₂4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H H CH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂ 4-OMe H HCH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ H H CH₂CF₃ CF₃ H Me HCH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me H CH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 5-Cl MeH CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me H CH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-BrMe H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃3-Br Me H CH₂CF₃ CF₃ 4-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me HCH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl Me H CH₂CF₃ CF(CF₃)₂ 4-Cl Me HCH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F MeH CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me HCH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃ CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CNMe H CH₂CF₃ CF(CF₃)₂ 4-CN Me H CH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂4-Me Me H CH₂CF₃ CF(CF₃)₂ 3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ Me H CH₂CF₃ CF₃ H H HCH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 4-Cl H HCH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃ 3-F, 4-F H H CH₂-2-Py CF₃3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-Py CF₃ 4-CF₃ H H CH₂-2-Py CF₃3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ HH CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H HCH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 4-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF₃ H HCH₂-2-Py CF(CF₃)₂ H H H CH₂-2-Py CF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-Py CF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H HCH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-Py CF(CF₃)₂ 3-CF₃ H H CH₂-2-PyCF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br,4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-Py CF(CF₃)₂ 4-Br H H CH₂-2-PyCF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H H CH₂-2-Py CF(CF₃)₂ 3-CN H HCH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂ 3-Me H H CH₂-2-Py CF(CF₃)₂4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-Py CF(CF₃)₂ 4-OMe H HCH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ H H CH₂-2-Py CF₃ HMe H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 4-Cl MeH CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H CH₂-2-Py CF₃3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 4-CF₃ Me HCH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₃ 3-Br,5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₃ 3-Br Me H CH₂-2-PyCF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 4-I Me H CH₂-2-Py CF₃3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-Me Me H CH₂-2-Py CF₃4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMe Me H CH₂-2-Py CF₃3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-PyCF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-Py CF(CF₃)₂ 4-Cl MeH CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-F Me H CH₂-2-PyCF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-Py CF(CF₃)₂ 2-F, 4-FMe H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I MeH CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me H CH₂-2-PyCF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-Py CF(CF₃)₂ 4-Me MeH CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMe Me H CH₂-2-PyCF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ Me H CH₂-2-Py

TABLE 5

  wherein m is 1, 2, 3, 4 or 5. R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H H CH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl,4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃ CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H HCH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H HCH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃ 4-I H H CH₂CF₃ CF₃ 3-CN H HCH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF₃ HH CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl HH CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H HCH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 4-CF₃ H H CH₂CF₃ CF(CF₃)₂3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br H HCH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br H H CH₂CF₃ CF(CF₃)₂4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H H CH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂ 4-OMe H HCH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ H H CH₂CF₃ CF₃ H Me HCH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me H CH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 5-Cl MeH CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me H CH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-BrMe H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃3-Br Me H CH₂CF₃ CF₃ 4-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me HCH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl Me H CH₂CF₃ CF(CF₃)₂ 4-Cl Me HCH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F MeH CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me HCH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃ CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CNMe H CH₂CF₃ CF(CF₃)₂ 4-CN Me H CH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂4-Me Me H CH₂CF₃ CF(CF₃)₂ 3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-OCF₃ Me H CH₂CF₃ CF₃ H H HCH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 4-Cl H HCH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃ 3-F, 4-F H H CH₂-2-Py CF₃3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-Py CF₃ 4-CF₃ H H CH₂-2-Py CF₃3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ HH CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H HCH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 4-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF₃ H HCH₂-2-Py CF(CF₃)₂ H H H CH₂-2-Py CF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-Py CF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H HCH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-Py CF(CF₃)₂ 3-CF₃ H H CH₂-2-PyCF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br,4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-Py CF(CF₃)₂ 4-Br H H CH₂-2-PyCF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H H CH₂-2-Py CF(CF₃)₂ 3-CN H HCH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂ 3-Me H H CH₂-2-Py CF(CF₃)₂4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-Py CF(CF₃)₂ 4-OMe H HCH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ H H CH₂-2-Py CF₃ HMe H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 4-Cl MeH CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H CH₂-2-Py CF₃3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 4-CF₃ Me HCH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-Br Me H CH₂-2-Py CF₃ 3-Br,5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-Py CF₃ 3-Br Me H CH₂-2-PyCF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 4-I Me H CH₂-2-Py CF₃3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-Me Me H CH₂-2-Py CF₃4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMe Me H CH₂-2-Py CF₃3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-PyCF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-Py CF(CF₃)₂ 4-Cl MeH CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-F Me H CH₂-2-PyCF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-Py CF(CF₃)₂ 2-F, 4-FMe H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I MeH CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me H CH₂-2-PyCF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-Py CF(CF₃)₂ 4-Me MeH CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMe Me H CH₂-2-PyCF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF₃ Me H CH₂-2-Py

TABLE 6

R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃ CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H HCH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H HCH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃ 2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H H CH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H H CH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃,5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃ 3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H HCH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃ 4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃4-I H H CH₂CF₃ CF₃ 3-CN H H CH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H HCH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃ 3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF3 H H CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl H H CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂ 2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F HH CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H H CH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ HH CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃CF(CF₃)₂ 3-Br, 5-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂3-Br H H CH₂CF₃ CF(CF₃)₂ 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂ 3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H HCH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃ CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMeH H CH₂CF₃ CF(CF₃)₂ 4-OMe H H CH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂4-OCF3 H H CH₂CF₃ CF₃ H Me H CH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me HCH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃ CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl MeH CH₂CF₃ CF₃ 3-Cl, 5-Cl Me H CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me HCH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃ 2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me HCH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃ CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me HCH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-Br Me H CH₂CF₃ CF₃ 3-Br, 5-Br Me HCH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃ 3-Br Me H CH₂CF₃ CF₃ 4-Br Me HCH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me H CH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃ CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe MeH CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃ 3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF3 Me HCH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃ CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl MeH CH₂CF₃ CF(CF₃)₂ 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F Me H CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CN Me H CH₂CF₃ CF(CF₃)₂ 4-CN Me HCH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂ 4-Me Me H CH₂CF₃ CF(CF₃)₂3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃ CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃CF(CF₃)₂ 4-OCF3 Me H CH₂CF₃ CF₃ H H H CH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃3-Cl H H CH₂-2-Py CF₃ 4-Cl H H CH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-PyCF₃ 3-F H H CH₂-2-Py CF₃ 4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃3-F, 4-F H H CH₂-2-Py CF₃ 3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-PyCF₃ 4-CF₃ H H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H HCH₂-2-Py CF₃ 3-Cl, 4-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃3-Br, 5-Br H H CH₂-2-Py CF₃ 3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H HCH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃ 3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-PyCF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H H CH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃4-Me H H CH₂-2-Py CF₃ 3-OMe H H CH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF3 H H CH₂-2-Py CF(CF₃)₂ H H H CH₂-2-PyCF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H HCH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-PyCF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂ 4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F HH CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-PyCF(CF₃)₂ 3-CF₃ H H CH₂-2-Py CF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃,5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-BrH H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-PyCF(CF₃)₂ 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H HCH₂-2-Py CF(CF₃)₂ 3-CN H H CH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂3-Me H H CH₂-2-Py CF(CF₃)₂ 4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-PyCF(CF₃)₂ 4-OMe H H CH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF3H H CH₂-2-Py CF₃ H Me H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me HCH₂-2-Py CF₃ 4-Cl Me H CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl,4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-PyCF₃ 3-F Me H CH₂-2-Py CF₃ 4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me HCH₂-2-Py CF₃ 4-CF₃ Me H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃3-Cl, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-BrMe H CH₂-2-Py CF₃ 3-Br, 5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-PyCF₃ 3-Br Me H CH₂-2-Py CF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃4-I Me H CH₂-2-Py CF₃ 3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-MeMe H CH₂-2-Py CF₃ 4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMeMe H CH₂-2-Py CF₃ 3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF3 Me H CH₂-2-Py CF(CF₃)₂H Me H CH₂-2-Py CF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-PyCF(CF₃)₂ 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-FMe H CH₂-2-Py CF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-PyCF(CF₃)₂ 2-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂3-F, 5-F Me H CH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me HCH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me HCH₂-2-Py CF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-I Me H CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me HCH₂-2-Py CF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-PyCF(CF₃)₂ 4-Me Me H CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMeMe H CH₂-2-Py CF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF3 Me HCH₂-2-Py

TABLE 7

R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ H H H CH₂CF₃ CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl H HCH₂CF₃ CF₃ 4-Cl H H CH₂CF₃ CF₃ 2-Cl, 4-Cl H H CH₂CF₃ CF₃ 3-Cl, 4-Cl H HCH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃ 2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃CF₃ 4-F H H CH₂CF₃ CF₃ 2-F, 4-F H H CH₂CF₃ CF₃ 3-F, 4-F H H CH₂CF₃ CF₃3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H H CH₂CF₃ CF₃ 4-CF₃ H H CH₂CF₃ CF₃ 3-CF₃,5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ H H CH₂CF₃ CF₃ 3-Cl, 4-CF₃ H H CH₂CF₃CF₃ 3-Cl, 4-Br H H CH₂CF₃ CF₃ 3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br, 4-Br H HCH₂CF₃ CF₃ 3-Br H H CH₂CF₃ CF₃ 4-Br H H CH₂CF₃ CF₃ 3-I H H CH₂CF₃ CF₃4-I H H CH₂CF₃ CF₃ 3-CN H H CH₂CF₃ CF₃ 4-CN H H CH₂CF₃ CF₃ 3-Me H HCH₂CF₃ CF₃ 4-Me H H CH₂CF₃ CF₃ 3-OMe H H CH₂CF₃ CF₃ 4-OMe H H CH₂CF₃ CF₃3-OCF₃ H H CH₂CF₃ CF₃ 4-OCF3 H H CH₂CF₃ CF(CF₃)₂ H H H CH₂CF₃ CF(CF₃)₂2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl H H CH₂CF₃ CF(CF₃)₂ 4-Cl H H CH₂CF₃CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CF₃ CF(CF₃)₂3-Cl, 5-Cl H H CH₂CF₃ CF(CF₃)₂ 2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃CF(CF₃)₂ 4-F H H CH₂CF₃ CF(CF₃)₂ 2-F, 4-F H H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F HH CH₂CF₃ CF(CF₃)₂ 3-F, 5-F H H CH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ HH CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br H H CH₂CF₃CF(CF₃)₂ 3-Br, 5-Br H H CH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br H H CH₂CF₃ CF(CF₃)₂3-Br H H CH₂CF₃ CF(CF₃)₂ 4-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃CF(CF₃)₂ 4-I H H CH₂CF₃ CF(CF₃)₂ 3-CN H H CH₂CF₃ CF(CF₃)₂ 4-CN H HCH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃ CF(CF₃)₂ 4-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMeH H CH₂CF₃ CF(CF₃)₂ 4-OMe H H CH₂CF₃ CF(CF₃)₂ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂4-OCF3 H H CH₂CF₃ CF₃ H Me H CH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-Cl Me HCH₂CF₃ CF₃ 4-Cl Me H CH₂CF₃ CF₃ 2-Cl, 4-Cl Me H CH₂CF₃ CF₃ 3-Cl, 4-Cl MeH CH₂CF₃ CF₃ 3-Cl, 5-Cl Me H CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me HCH₂CF₃ CF₃ 4-F Me H CH₂CF₃ CF₃ 2-F, 4-F Me H CH₂CF₃ CF₃ 3-F, 4-F Me HCH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃ CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 4-CF₃ Me HCH₂CF₃ CF₃ 3-CF₃, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃3-Cl, 4-CF₃ Me H CH₂CF₃ CF₃ 3-Cl, 4-Br Me H CH₂CF₃ CF₃ 3-Br, 5-Br Me HCH₂CF₃ CF₃ 3-Br, 4-Br Me H CH₂CF₃ CF₃ 3-Br Me H CH₂CF₃ CF₃ 4-Br Me HCH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 4-I Me H CH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃4-CN Me H CH₂CF₃ CF₃ 3-Me Me H CH₂CF₃ CF₃ 4-Me Me H CH₂CF₃ CF₃ 3-OMe MeH CH₂CF₃ CF₃ 4-OMe Me H CH₂CF₃ CF₃ 3-OCF₃ Me H CH₂CF₃ CF₃ 4-OCF3 Me HCH₂CF₃ CF(CF₃)₂ H Me H CH₂CF₃ CF(CF₃)₂ 2-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl MeH CH₂CF₃ CF(CF₃)₂ 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂CF₃CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CF₃ CF(CF₃)₂2-F Me H CH₂CF₃ CF(CF₃)₂ 3-F Me H CH₂CF₃ CF(CF₃)₂ 4-F Me H CH₂CF₃CF(CF₃)₂ 2-F, 4-F Me H CH₂CF₃ CF(CF₃)₂ 3-F, 4-F Me H CH₂CF₃ CF(CF₃)₂3-F, 5-F Me H CH₂CF₃ CF(CF₃)₂ 3-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 4-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ Me HCH₂CF₃ CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Br Me H CH₂CF₃CF(CF₃)₂ 3-Br, 5-Br Me H CH₂CF₃ CF(CF₃)₂ 3-Br, 4-Br Me H CH₂CF₃ CF(CF₃)₂3-Br Me H CH₂CF₃ CF(CF₃)₂ 4-Br Me H CH₂CF₃ CF(CF₃)₂ 3-I Me H CH₂CF₃CF(CF₃)₂ 4-I Me H CH₂CF₃ CF(CF₃)₂ 3-CN Me H CH₂CF₃ CF(CF₃)₂ 4-CN Me HCH₂CF₃ CF(CF₃)₂ 3-Me Me H CH₂CF₃ CF(CF₃)₂ 4-Me Me H CH₂CF₃ CF(CF₃)₂3-OMe Me H CH₂CF₃ CF(CF₃)₂ 4-OMe Me H CH₂CF₃ CF(CF₃)₂ 3-OCF₃ Me H CH₂CF₃CF(CF₃)₂ 4-OCF3 Me H CH₂CF₃ CF₃ H H H CH₂-2-Py CF₃ 2-Cl H H CH₂-2-Py CF₃3-Cl H H CH₂-2-Py CF₃ 4-Cl H H CH₂-2-Py CF₃ 2-Cl, 4-Cl H H CH₂-2-Py CF₃3-Cl, 4-Cl H H CH₂-2-Py CF₃ 3-Cl, 5-Cl H H CH₂-2-Py CF₃ 2-F H H CH₂-2-PyCF₃ 3-F H H CH₂-2-Py CF₃ 4-F H H CH₂-2-Py CF₃ 2-F, 4-F H H CH₂-2-Py CF₃3-F, 4-F H H CH₂-2-Py CF₃ 3-F, 5-F H H CH₂-2-Py CF₃ 3-CF₃ H H CH₂-2-PyCF₃ 4-CF₃ H H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H HCH₂-2-Py CF₃ 3-Cl, 4-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 4-Br H H CH₂-2-Py CF₃3-Br, 5-Br H H CH₂-2-Py CF₃ 3-Br, 4-Br H H CH₂-2-Py CF₃ 3-Br H HCH₂-2-Py CF₃ 4-Br H H CH₂-2-Py CF₃ 3-I H H CH₂-2-Py CF₃ 4-I H H CH₂-2-PyCF₃ 3-CN H H CH₂-2-Py CF₃ 4-CN H H CH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃4-Me H H CH₂-2-Py CF₃ 3-OMe H H CH₂-2-Py CF₃ 4-OMe H H CH₂-2-Py CF₃3-OCF₃ H H CH₂-2-Py CF₃ 4-OCF3 H H CH₂-2-Py CF(CF₃)₂ H H H CH₂-2-PyCF(CF₃)₂ 2-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl H H CH₂-2-Py CF(CF₃)₂ 4-Cl H HCH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H HCH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-2-Py CF(CF₃)₂ 2-F H H CH₂-2-PyCF(CF₃)₂ 3-F H H CH₂-2-Py CF(CF₃)₂ 4-F H H CH₂-2-Py CF(CF₃)₂ 2-F, 4-F HH CH₂-2-Py CF(CF₃)₂ 3-F, 4-F H H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F H H CH₂-2-PyCF(CF₃)₂ 3-CF₃ H H CH₂-2-Py CF(CF₃)₂ 4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-CF₃,5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl,4-CF₃ H H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-BrH H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-Br H H CH₂-2-PyCF(CF₃)₂ 4-Br H H CH₂-2-Py CF(CF₃)₂ 3-I H H CH₂-2-Py CF(CF₃)₂ 4-I H HCH₂-2-Py CF(CF₃)₂ 3-CN H H CH₂-2-Py CF(CF₃)₂ 4-CN H H CH₂-2-Py CF(CF₃)₂3-Me H H CH₂-2-Py CF(CF₃)₂ 4-Me H H CH₂-2-Py CF(CF₃)₂ 3-OMe H H CH₂-2-PyCF(CF₃)₂ 4-OMe H H CH₂-2-Py CF(CF₃)₂ 3-OCF₃ H H CH₂-2-Py CF(CF₃)₂ 4-OCF3H H CH₂-2-Py CF₃ H Me H CH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me HCH₂-2-Py CF₃ 4-Cl Me H CH₂-2-Py CF₃ 2-Cl, 4-Cl Me H CH₂-2-Py CF₃ 3-Cl,4-Cl Me H CH₂-2-Py CF₃ 3-Cl, 5-Cl Me H CH₂-2-Py CF₃ 2-F Me H CH₂-2-PyCF₃ 3-F Me H CH₂-2-Py CF₃ 4-F Me H CH₂-2-Py CF₃ 2-F, 4-F Me H CH₂-2-PyCF₃ 3-F, 4-F Me H CH₂-2-Py CF₃ 3-F, 5-F Me H CH₂-2-Py CF₃ 3-CF₃ Me HCH₂-2-Py CF₃ 4-CF₃ Me H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃3-Cl, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF₃ 3-Cl, 4-BrMe H CH₂-2-Py CF₃ 3-Br, 5-Br Me H CH₂-2-Py CF₃ 3-Br, 4-Br Me H CH₂-2-PyCF₃ 3-Br Me H CH₂-2-Py CF₃ 4-Br Me H CH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃4-I Me H CH₂-2-Py CF₃ 3-CN Me H CH₂-2-Py CF₃ 4-CN Me H CH₂-2-Py CF₃ 3-MeMe H CH₂-2-Py CF₃ 4-Me Me H CH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 4-OMeMe H CH₂-2-Py CF₃ 3-OCF₃ Me H CH₂-2-Py CF₃ 4-OCF3 Me H CH₂-2-Py CF(CF₃)₂H Me H CH₂-2-Py CF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl Me H CH₂-2-PyCF(CF₃)₂ 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂3-Cl, 4-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-FMe H CH₂-2-Py CF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 4-F Me H CH₂-2-PyCF(CF₃)₂ 2-F, 4-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 4-F Me H CH₂-2-Py CF(CF₃)₂3-F, 5-F Me H CH₂-2-Py CF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-CF₃ Me HCH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-CF₃ Me HCH₂-2-Py CF(CF₃)₂ 3-Cl, 4-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Br Me HCH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 4-Br Me HCH₂-2-Py CF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 4-Br Me H CH₂-2-PyCF(CF₃)₂ 3-I Me H CH₂-2-Py CF(CF₃)₂ 4-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN Me HCH₂-2-Py CF(CF₃)₂ 4-CN Me H CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-PyCF(CF₃)₂ 4-Me Me H CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-Py CF(CF₃)₂ 4-OMeMe H CH₂-2-Py CF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py CF(CF₃)₂ 4-OCF3 Me HCH₂-2-Py

TABLE 8

R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ 3-Cl, 4-Cl H H H CF₃ 3-Cl, 4-Cl H H Me CF₃3-Cl, 4-Cl H H Et CF₃ 3-Cl, 4-Cl H H i-Pr CF₃ 3-Cl, 4-Cl H H CH₂Ph CF₃3-Cl, 4-Cl H H CH₂CO₂Me CF₃ 3-Cl, 4-Cl H H CH₂CN CF₃ 3-Cl, 4-Cl H HCH₂-2-thiazolyl CF₃ 3-Cl, 4-Cl H H CH₂-4-thiazolyl CF₃ 3-Cl, 4-Cl H HCH₂-5-thiazolyl CF₃ 3-Cl, 4-Cl H H CH₂-3-Py CF₃ 3-Cl, 4-Cl H H CH₂-4-PyCF₃ 3-Cl, 4-Cl H Me CH₂CF₃ CF₃ 3-Cl, 4-Cl H CO₂Me CH₂CF₃ CF₃ 3-Cl, 4-ClH C(O)Me CH₂CF₃ CF₃ 3-Cl, 4-Cl H Me CH₂-2-Py CF₃ 3-Cl, 4-Cl H CO₂MeCH₂-2-Py CF₃ 3-Cl, 4-Cl H C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H H HCF(CF₃)₂ 3-Cl, 4-Cl H H Me CF(CF₃)₂ 3-Cl, 4-Cl H H Et CF(CF₃)₂ 3-Cl,4-Cl H H i-Pr CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂Ph CF(CF₃)₂ 3-Cl, 4-Cl H HCH₂CO₂Me CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂CN CF(CF₃)₂ 3-Cl, 4-Cl H HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,4-Cl H H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 4-Cl H H CH₂-3-Py CF(CF₃)₂ 3-Cl,4-Cl H H CH₂-4-Py CF(CF₃)₂ 3-Cl, 4-Cl H Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl HCO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl H C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl HMe CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl H CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl HC(O)Me CH₂-2-Py CF₃ 3-Cl, 4-Cl Me H H CF₃ 3-Cl, 4-Cl Me H Me CF₃ 3-Cl,4-Cl Me H Et CF₃ 3-Cl, 4-Cl Me H i-Pr CF₃ 3-Cl, 4-Cl Me H CH₂Ph CF₃3-Cl, 4-Cl Me H CH₂CO₂Me CF₃ 3-Cl, 4-Cl Me H CH₂CN CF₃ 3-Cl, 4-Cl Me HCH₂-2-thiazolyl CF₃ 3-Cl, 4-Cl Me H CH₂-4-thiazolyl CF₃ 3-Cl, 4-Cl Me HCH₂-5-thiazolyl CF₃ 3-Cl, 4-Cl Me H CH₂-3-Py CF₃ 3-Cl, 4-Cl Me HCH₂-4-Py CF₃ 3-Cl, 4-Cl Me Me CH₂CF₃ CF₃ 3-Cl, 4-Cl Me CO₂Me CH₂CF₃ CF₃3-Cl, 4-Cl Me C(O)Me CH₂CF₃ CF₃ 3-Cl, 4-Cl Me Me CH₂-2-Py CF₃ 3-Cl, 4-ClMe CO₂Me CH₂-2-Py CF₃ 3-Cl, 4-Cl Me C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-ClMe H H CF(CF₃)₂ 3-Cl, 4-Cl Me H Me CF(CF₃)₂ 3-Cl, 4-Cl Me H Et CF(CF₃)₂3-Cl, 4-Cl Me H i-Pr CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂Ph CF(CF₃)₂ 3-Cl, 4-ClMe H CH₂CO₂Me CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂CN CF(CF₃)₂ 3-Cl, 4-Cl Me HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,4-Cl Me H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 4-Cl Me H CH₂-3-Py CF(CF₃)₂3-Cl, 4-Cl Me H CH₂-4-Py CF(CF₃)₂ 3-Cl, 4-Cl Me Me CH₂CF₃ CF(CF₃)₂ 3-Cl,4-Cl Me CO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 4-Cl Me C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl,4-Cl Me Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 4-Cl Me CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl,4-Cl Me C(O)Me CH₂-2-Py CF₃ 3-Cl, 5-Cl H H H CF₃ 3-Cl, 5-Cl H H Me CF₃3-Cl, 5-Cl H H Et CF₃ 3-Cl, 5-Cl H H i-Pr CF₃ 3-Cl, 5-Cl H H CH₂Ph CF₃3-Cl, 5-Cl H H CH₂CO₂Me CF₃ 3-Cl, 5-Cl H H CH₂CN CF₃ 3-Cl, 5-Cl H HCH₂-2-thiazolyl CF₃ 3-Cl, 5-Cl H H CH₂-4-thiazolyl CF₃ 3-Cl, 5-Cl H HCH₂-5-thiazolyl CF₃ 3-Cl, 5-Cl H H CH₂-3-Py CF₃ 3-Cl, 5-Cl H H CH₂-4-PyCF₃ 3-Cl, 5-Cl H Me CH₂CF₃ CF₃ 3-Cl, 5-Cl H CO₂Me CH₂CF₃ CF₃ 3-Cl, 5-ClH C(O)Me CH₂CF₃ CF₃ 3-Cl, 5-Cl H Me CH₂-2-Py CF₃ 3-Cl, 5-Cl H CO₂MeCH₂-2-Py CF₃ 3-Cl, 5-Cl H C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H H HCF(CF₃)₂ 3-Cl, 5-Cl H H Me CF(CF₃)₂ 3-Cl, 5-Cl H H Et CF(CF₃)₂ 3-Cl,5-Cl H H i-Pr CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂Ph CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂CO₂Me CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CN CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,5-Cl H H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-3-Py CF(CF₃)₂ 3-Cl,5-Cl H H CH₂-4-Py CF(CF₃)₂ 3-Cl, 5-Cl H Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl HCO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl HMe CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl HC(O)Me CH₂-2-Py CF₃ 3-Cl, 5-Cl Me H H CF₃ 3-Cl, 5-Cl Me H Me CF₃ 3-Cl,5-Cl Me H Et CF₃ 3-Cl, 5-Cl Me H i-Pr CF₃ 3-Cl, 5-Cl Me H CH₂Ph CF₃3-Cl, 5-Cl Me H CH₂CO₂Me CF₃ 3-Cl, 5-Cl Me H CH₂CN CF₃ 3-Cl, 5-Cl Me HCH₂-2-thiazolyl CF₃ 3-Cl, 5-Cl Me H CH₂-4-thiazolyl CF₃ 3-Cl, 5-Cl Me HCH₂-5-thiazolyl CF₃ 3-Cl, 5-Cl Me H CH₂-3-Py CF₃ 3-Cl, 5-Cl Me HCH₂-4-Py CF₃ 3-Cl, 5-Cl Me Me CH₂CF₃ CF₃ 3-Cl, 5-Cl Me CO₂Me CH₂CF₃ CF₃3-Cl, 5-Cl Me C(O)Me CH₂CF₃ CF₃ 3-Cl, 5-Cl Me Me CH₂-2-Py CF₃ 3-Cl, 5-ClMe CO₂Me CH₂-2-Py CF₃ 3-Cl, 5-Cl Me C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-ClMe H H CF(CF₃)₂ 3-Cl, 5-Cl Me H Me CF(CF₃)₂ 3-Cl, 5-Cl Me H Et CF(CF₃)₂3-Cl, 5-Cl Me H i-Pr CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂Ph CF(CF₃)₂ 3-Cl, 5-ClMe H CH₂CO₂Me CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CN CF(CF₃)₂ 3-Cl, 5-Cl Me HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,5-Cl Me H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-3-Py CF(CF₃)₂3-Cl, 5-Cl Me H CH₂-4-Py CF(CF₃)₂ 3-Cl, 5-Cl Me Me CH₂CF₃ CF(CF₃)₂ 3-Cl,5-Cl Me CO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl Me C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl,5-Cl Me Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl,5-Cl Me C(O)Me CH₂-2-Py

TABLE 9

R¹ (R²)_(m) R³ R⁴ R⁵ CF₃ 3-Cl H H H CF₃ 3-Cl H H Me CF₃ 3-Cl H H Et CF₃3-Cl H H i-Pr CF₃ 3-Cl H H CH₂Ph CF₃ 3-Cl H H CH₂CO₂Me CF₃ 3-Cl H HCH₂CN CF₃ 3-Cl H H CH₂-2-thiazolyl CF₃ 3-Cl H H CH₂-4-thiazolyl CF₃ 3-ClH H CH₂-5-thiazolyl CF₃ 3-Cl H H CH₂-3-Py CF₃ 3-Cl H H CH₂-4-Py CF₃ 3-ClH Me CH₂CF₃ CF₃ 3-Cl H CO₂Me CH₂CF₃ CF₃ 3-Cl H C(O)Me CH₂CF₃ CF₃ 3-Cl HMe CH₂-2-Py CF₃ 3-Cl H CO₂Me CH₂-2-Py CF₃ 3-Cl H C(O)Me CH₂-2-PyCF(CF₃)₂ 3-Cl H H H CF(CF₃)₂ 3-Cl H H Me CF(CF₃)₂ 3-Cl H H Et CF(CF₃)₂3-Cl H H i-Pr CF(CF₃)₂ 3-Cl H H CH₂Ph CF(CF₃)₂ 3-Cl H H CH₂CO₂MeCF(CF₃)₂ 3-Cl H H CH₂CN CF(CF₃)₂ 3-Cl H H CH₂-2-thiazolyl CF(CF₃)₂ 3-ClH H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl H H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl H HCH₂-3-Py CF(CF₃)₂ 3-Cl H H CH₂-4-Py CF(CF₃)₂ 3-Cl H Me CH₂CF₃ CF(CF₃)₂3-Cl H CO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl H C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl H MeCH₂-2-Py CF(CF₃)₂ 3-Cl H CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl H C(O)Me CH₂-2-PyCF₃ 3-Cl Me H H CF₃ 3-Cl Me H Me CF₃ 3-Cl Me H Et CF₃ 3-Cl Me H i-Pr CF₃3-Cl Me H CH₂Ph CF₃ 3-Cl Me H CH₂CO₂Me CF₃ 3-Cl Me H CH₂CN CF₃ 3-Cl Me HCH₂-2-thiazolyl CF₃ 3-Cl Me H CH₂-4-thiazolyl CF₃ 3-Cl Me HCH₂-5-thiazolyl CF₃ 3-Cl Me H CH₂-3-Py CF₃ 3-Cl Me H CH₂-4-Py CF₃ 3-ClMe Me CH₂CF₃ CF₃ 3-Cl Me CO₂Me CH₂CF₃ CF₃ 3-Cl Me C(O)Me CH₂CF₃ CF₃ 3-ClMe Me CH₂-2-Py CF₃ 3-Cl Me CO₂Me CH₂-2-Py CF₃ 3-Cl Me C(O)Me CH₂-2-PyCF(CF₃)₂ 3-Cl Me H H CF(CF₃)₂ 3-Cl Me H Me CF(CF₃)₂ 3-Cl Me H EtCF(CF₃)₂ 3-Cl Me H i-Pr CF(CF₃)₂ 3-Cl Me H CH₂Ph CF(CF₃)₂ 3-Cl Me HCH₂CO₂Me CF(CF₃)₂ 3-Cl Me H CH₂CN CF(CF₃)₂ 3-Cl Me H CH₂-2-thiazolylCF(CF₃)₂ 3-Cl Me H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl Me H CH₂-5-thiazolylCF(CF₃)₂ 3-Cl Me H CH₂-3-Py CF(CF₃)₂ 3-Cl Me H CH₂-4-Py CF(CF₃)₂ 3-Cl MeMe CH₂CF₃ CF(CF₃)₂ 3-Cl Me CO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl Me C(O)Me CH₂CF₃CF(CF₃)₂ 3-Cl Me Me CH₂-2-Py CF(CF₃)₂ 3-Cl Me CO₂Me CH₂-2-Py CF(CF₃)₂3-Cl Me C(O)Me CH₂-2-Py CF₃ H H H CH₂CF₃ CF₃ 2-Cl H H CH₂CF₃ CF₃ 3-Cl HH CH₂CF₃ CF₃ 3-Cl, 5-Cl H H CH₂CF₃ CF₃ 2-F H H CH₂CF₃ CF₃ 3-F H H CH₂CF₃CF₃ 3-F, 5-F H H CH₂CF₃ CF₃ 3-CF₃ H H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃CF₃ 3-Cl, 5-CF₃ H H CH₂CF₃ CF₃ 3-Br, 5-Br H H CH₂CF₃ CF₃ 3-Br H H CH₂CF₃CF₃ 3-I H H CH₂CF₃ CF₃ 3-CN H H CH₂CF₃ CF₃ 3-Me H H CH₂CF₃ CF₃ 3-OMe H HCH₂CF₃ CF₃ 3-OCF₃ H H CH₂CF₃ CF₃ H Cl H CH₂CF₃ CF₃ 2-Cl Cl H CH₂CF₃ CF₃3-Cl Cl H CH₂CF₃ CF₃ 3-Cl, 5-Cl Cl H CH₂CF₃ CF₃ 2-F Cl H CH₂CF₃ CF₃ 3-FCl H CH₂CF₃ CF₃ 3-F, 5-F Cl H CH₂CF₃ CF₃ 3-CF₃ Cl H CH₂CF₃ CF₃ 3-CF₃,5-CF₃ Cl H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Cl H CH₂CF₃ CF₃ 3-Br, 5-Br Cl H CH₂CF₃CF₃ 3-Br Cl H CH₂CF₃ CF₃ 3-I Cl H CH₂CF₃ CF₃ 3-CN Cl H CH₂CF₃ CF₃ 3-MeCl H CH₂CF₃ CF₃ 3-OMe Cl H CH₂CF₃ CF₃ 3-OCF₃ Cl H CH₂CF₃ CF₃ H Me HCH₂-2-Py CF₃ 2-Cl Me H CH₂-2-Py CF₃ 3-Cl Me H CH₂-2-Py CF₃ 3-Cl, 5-Cl MeH CH₂-2-Py CF₃ 2-F Me H CH₂-2-Py CF₃ 3-F Me H CH₂-2-Py CF₃ 3-F, 5-F Me HCH₂-2-Py CF₃ 3-CF₃ Me H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-Py CF₃3-Cl, 5-CF₃ Me H CH₂-2-Py CF₃ 3-Br, 5-Br Me H CH₂-2-Py CF₃ 3-Br Me HCH₂-2-Py CF₃ 3-I Me H CH₂-2-Py CF₃ 3-CN Me H CH₂-2-Py CF₃ 3-Me Me HCH₂-2-Py CF₃ 3-OMe Me H CH₂-2-Py CF₃ 3-OCF₃ Me H CH₂-2-Py CF₂CF₃ H H HCH₂CF₃ CF₂CF₃ 2-Cl H H CH₂CF₃ CF₂CF₃ 3-Cl H H CH₂CF₃ CF₂CF₃ 3-Cl, 5-Cl HH CH₂CF₃ CF₂CF₃ 2-F H H CH₂CF₃ CF₂CF₃ 3-F H H CH₂CF₃ CF₂CF₃ 3-F, 5-F H HCH₂CF₃ CF₂CF₃ 3-CF₃ H H CH₂CF₃ CF₂CF₃ 3-CF₃, 5-CF₃ H H CH₂CF₃ CF₂CF₃3-Cl, 5-CF₃ H H CH₂CF₃ CF₂CF₃ 3-Br, 5-Br H H CH₂CF₃ CF₂CF₃ 3-Br H HCH₂CF₃ CF₂CF₃ 3-I H H CH₂CF₃ CF₂CF₃ 3-CN H H CH₂CF₃ CF₂CF₃ 3-Me H HCH₂CF₃ CF₂CF₃ 3-OMe H H CH₂CF₃ CF₂CF₃ 3-OCF₃ H H CH₂CF₃ CF(CF₃)₂ H H HCH₂CF₃ CF(CF₃)₂ 2-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl H H CH₂CF₃ CF(CF₃)₂ 3-Cl,5-Cl H H CH₂CF₃ CF(CF₃)₂ 2-F H H CH₂CF₃ CF(CF₃)₂ 3-F H H CH₂CF₃ CF(CF₃)₂3-F, 5-F H H CH₂CF₃ CF(CF₃)₂ 3-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-CF₃, 5-CF₃ H HCH₂CF₃ CF(CF₃)₂ 3-Cl, 5-CF₃ H H CH₂CF₃ CF(CF₃)₂ 3-Br, 5-Br H H CH₂CF₃CF(CF₃)₂ 3-Br H H CH₂CF₃ CF(CF₃)₂ 3-I H H CH₂CF₃ CF(CF₃)₂ 3-CN H HCH₂CF₃ CF(CF₃)₂ 3-Me H H CH₂CF₃ CF(CF₃)₂ 3-OMe H H CH₂CF₃ CF(CF₃)₂3-OCF₃ H H CH₂CF₃ CF₃ 3-Cl, 5-Cl H H H CF₃ 3-Cl, 5-Cl H H Me CF₃ 3-Cl,5-Cl H H Et CF₃ 3-Cl, 5-Cl H H i-Pr CF₃ 3-Cl, 5-Cl H H CH₂Ph CF₃ 3-Cl,5-Cl H H CH₂CO₂Me CF₃ 3-Cl, 5-Cl H H CH₂CN CF₃ 3-Cl, 5-Cl H HCH₂-2-thiazolyl CF₃ 3-Cl, 5-Cl H H CH₂-4-thiazolyl CF₃ 3-Cl, 5-Cl H HCH₂-5-thiazolyl CF₃ 3-Cl, 5-Cl H H CH₂-3-Py CF₃ 3-Cl, 5-Cl H H CH₂-4-PyCF₃ 3-Cl, 5-Cl H Me CH₂CF₃ CF₃ 3-Cl, 5-Cl H CO₂Me CH₂CF₃ CF₃ 3-Cl, 5-ClH C(O)Me CH₂CF₃ CF₃ 3-Cl, 5-Cl H Me CH₂-2-Py CF₃ 3-Cl, 5-Cl H CO₂MeCH₂-2-Py CF₃ 3-Cl, 5-Cl H C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H H HCF(CF₃)₂ 3-Cl, 5-Cl H H Me CF(CF₃)₂ 3-Cl, 5-Cl H H Et CF(CF₃)₂ 3-Cl,5-Cl H H i-Pr CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂Ph CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂CO₂Me CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂CN CF(CF₃)₂ 3-Cl, 5-Cl H HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,5-Cl H H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl H H CH₂-3-Py CF(CF₃)₂ 3-Cl,5-Cl H H CH₂-4-Py CF(CF₃)₂ 3-Cl, 5-Cl H Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl HCO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl H C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl HMe CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl H CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl HC(O)Me CH₂-2-Py CF₃ 3-Cl, 5-Cl Me H H CF₃ 3-Cl, 5-Cl Me H Me CF₃ 3-Cl,5-Cl Me H Et CF₃ 3-Cl, 5-Cl Me H i-Pr CF₃ 3-Cl, 5-Cl Me H CH₂Ph CF₃3-Cl, 5-Cl Me H CH₂CO₂Me CF₃ 3-Cl, 5-Cl Me H CH₂CN CF₃ 3-Cl, 5-Cl Me HCH₂-2-thiazolyl CF₃ 3-Cl, 5-Cl Me H CH₂-4-thiazolyl CF₃ 3-Cl, 5-Cl Me HCH₂-5-thiazolyl CF₃ 3-Cl, 5-Cl Me H CH₂-3-Py CF₃ 3-Cl, 5-Cl Me HCH₂-4-Py CF₃ 3-Cl, 5-Cl Me Me CH₂CF₃ CF₃ 3-Cl, 5-Cl Me CO₂Me CH₂CF₃ CF₃3-Cl, 5-Cl Me C(O)Me CH₂CF₃ CF₃ 3-Cl, 5-Cl Me Me CH₂-2-Py CF₃ 3-Cl, 5-ClMe CO₂Me CH₂-2-Py CF₃ 3-Cl, 5-Cl Me C(O)Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-ClMe H H CF(CF₃)₂ 3-Cl, 5-Cl Me H Me CF(CF₃)₂ 3-Cl, 5-Cl Me H Et CF(CF₃)₂3-Cl, 5-Cl Me H i-Pr CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂Ph CF(CF₃)₂ 3-Cl, 5-ClMe H CH₂CO₂Me CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂CN CF(CF₃)₂ 3-Cl, 5-Cl Me HCH₂-2-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-4-thiazolyl CF(CF₃)₂ 3-Cl,5-Cl Me H CH₂-5-thiazolyl CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-3-Py CF(CF₃)₂3-Cl, 5-Cl Me H CH₂-4-Py CF(CF₃)₂ 3-Cl, 5-Cl Me Me CH₂CF₃ CF(CF₃)₂ 3-Cl,5-Cl Me CO₂Me CH₂CF₃ CF(CF₃)₂ 3-Cl, 5-Cl Me C(O)Me CH₂CF₃ CF(CF₃)₂ 3-Cl,5-Cl Me Me CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me CO₂Me CH₂-2-Py CF(CF₃)₂ 3-Cl,5-Cl Me C(O)Me CH₂-2-Py CF₃ H Me H CH₂CF₃ CF₃ 2-Cl Me H CH₂CF₃ CF₃ 3-ClMe H CH₂CF₃ CF₃ 3-Cl, 5-Cl Me H CH₂CF₃ CF₃ 2-F Me H CH₂CF₃ CF₃ 3-F Me HCH₂CF₃ CF₃ 3-F, 5-F Me H CH₂CF₃ CF₃ 3-CF₃ Me H CH₂CF₃ CF₃ 3-CF₃, 5-CF₃Me H CH₂CF₃ CF₃ 3-Cl, 5-CF₃ Me H CH₂CF₃ CF₃ 3-Br, 5-Br Me H CH₂CF₃ CF₃3-Br Me H CH₂CF₃ CF₃ 3-I Me H CH₂CF₃ CF₃ 3-CN Me H CH₂CF₃ CF₃ 3-Me Me HCH₂CF₃ CF₃ 3-OMe Me H CH₂CF₃ CF₃ 3-OCF₃ Me H CH₂CF₃ CF₃ H H H CH₂-2-PyCF₃ 2-Cl H H CH₂-2-Py CF₃ 3-Cl H H CH₂-2-Py CF₃ 3-Cl, 5-Cl H H CH₂-2-PyCF₃ 2-F H H CH₂-2-Py CF₃ 3-F H H CH₂-2-Py CF₃ 3-F, 5-F H H CH₂-2-Py CF₃3-CF₃ H H CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ H H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ H HCH₂-2-Py CF₃ 3-Br, 5-Br H H CH₂-2-Py CF₃ 3-Br H H CH₂-2-Py CF₃ 3-I H HCH₂-2-Py CF₃ 3-CN H H CH₂-2-Py CF₃ 3-Me H H CH₂-2-Py CF₃ 3-OMe H HCH₂-2-Py CF₃ 3-OCF₃ H H CH₂-2-Py CF₃ H Cl H CH₂-2-Py CF₃ 2-Cl Cl HCH₂-2-Py CF₃ 3-Cl Cl H CH₂-2-Py CF₃ 3-Cl, 5-Cl Cl H CH₂-2-Py CF₃ 2-F ClH CH₂-2-Py CF₃ 3-F Cl H CH₂-2-Py CF₃ 3-F, 5-F Cl H CH₂-2-Py CF₃ 3-CF₃ ClH CH₂-2-Py CF₃ 3-CF₃, 5-CF₃ Cl H CH₂-2-Py CF₃ 3-Cl, 5-CF₃ Cl H CH₂-2-PyCF₃ 3-Br, 5-Br Cl H CH₂-2-Py CF₃ 3-Br Cl H CH₂-2-Py CF₃ 3-I Cl HCH₂-2-Py CF₃ 3-CN Cl H CH₂-2-Py CF₃ 3-Me Cl H CH₂-2-Py CF₃ 3-OMe Cl HCH₂-2-Py CF₃ 3-OCF₃ Cl H CH₂-2-Py CF₂CF₃ H Me H CH₂-2-Py CF₂CF₃ 2-Cl MeH CH₂-2-Py CF₂CF₃ 3-Cl Me H CH₂-2-Py CF₂CF₃ 3-Cl, 5-Cl Me H CH₂-2-PyCF₂CF₃ 2-F Me H CH₂-2-Py CF₂CF₃ 3-F Me H CH₂-2-Py CF₂CF₃ 3-F, 5-F Me HCH₂-2-Py CF₂CF₃ 3-CF₃ Me H CH₂-2-Py CF₂CF₃ 3-CF₃, 5-CF₃ Me H CH₂-2-PyCF₂CF₃ 3-Cl, 5-CF₃ Me H CH₂-2-Py CF₂CF₃ 3-Br, 5-Br Me H CH₂-2-Py CF₂CF₃3-Br Me H CH₂-2-Py CF₂CF₃ 3-I Me H CH₂-2-Py CF₂CF₃ 3-CN Me H CH₂-2-PyCF₂CF₃ 3-Me Me H CH₂-2-Py CF₂CF₃ 3-OMe Me H CH₂-2-Py CF₂CF₃ 3-OCF₃ Me HCH₂-2-Py CF(CF₃)₂ H Me H CH₂-2-Py CF(CF₃)₂ 2-Cl Me H CH₂-2-Py CF(CF₃)₂3-Cl Me H CH₂-2-Py CF(CF₃)₂ 3-Cl, 5-Cl Me H CH₂-2-Py CF(CF₃)₂ 2-F Me HCH₂-2-Py CF(CF₃)₂ 3-F Me H CH₂-2-Py CF(CF₃)₂ 3-F, 5-F Me H CH₂-2-PyCF(CF₃)₂ 3-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-CF₃, 5-CF₃ Me H CH₂-2-PyCF(CF₃)₂ 3-Cl, 5-CF₃ Me H CH₂-2-Py CF(CF₃)₂ 3-Br, 5-Br Me H CH₂-2-PyCF(CF₃)₂ 3-Br Me H CH₂-2-Py CF(CF₃)₂ 3-I Me H CH₂-2-Py CF(CF₃)₂ 3-CN MeH CH₂-2-Py CF(CF₃)₂ 3-Me Me H CH₂-2-Py CF(CF₃)₂ 3-OMe Me H CH₂-2-PyCF(CF₃)₂ 3-OCF₃ Me H CH₂-2-Py

Formulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with a suitable carrier comprising at least one of a liquiddiluent, a solid diluent or a surfactant. The formulation or compositioningredients are selected to be consistent with the physical propertiesof the active ingredient, mode of application and environmental factorssuch as soil type, moisture and temperature. Useful formulations includeliquids such as solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions and/or suspoemulsions)and the like which optionally can be thickened into gels. Usefulformulations further include solids such as dusts, powders, granules,pellets, tablets, films (including seed coatings), and the like whichcan be water-dispersible (“wettable”) or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand 0.001-90 0-99.999 0-15 Water-soluble Granules, Tablets and Powders.Suspensions, Emulsions,    1-50 40-99    0-50 Solutions (includingEmulsifiable Concentrates) Dusts    1-25 70-99    0-5  Granules andPellets 0.001-99 5-99.999 0-15 High Strength   90-99 0-10    0-2 Compositions

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates,glycerol esters, poly-oxyethylene/polyoxypropylene block copolymers, andalkylpolyglycosides where the number of glucose units, referred to asdegree of polymerization (D.P.), can range from 1 to 3 and the alkylunits can range from C₆ to C₁₄ (see Pure and Applied Chemistry 72,1255-1264). Solid diluents include, for example, clays such asbentonite, montmorillonite, attapulgite and kaolin, starch, sugar,silica, talc, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Liquid diluents include,for example, water, N,N-dimethylformamide, dimethyl sulfoxide,N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylenecarbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes,glycerine, triacetine, oils of olive, castor, linseed, tung, sesame,corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acidesters, ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptylacetate and octyl acetate, and alcohols such as methanol, cyclohexanol,decanol, benzyl and tetrahydrofurfuryl alcohol.

Useful formulations of this invention may also contain materials wellknown to those skilled in the art as formulation aids such as antifoams,film formers and dyes. Antifoams can include water dispersible liquidscomprising polyorganosiloxanes like Rhodorsil® 416. The film formers caninclude polyvinyl acetates, polyvinyl acetate copolymers,polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols,polyvinyl alcohol copolymers and waxes. Dyes can include waterdispersible liquid colorant compositions like Pro-lzed® Colorant Red.One skilled in the art will appreciate that this is a non-exhaustivelist of formulation aids. Suitable examples of formulation aids includethose listed herein and those listed in McCutcheon's 2001, Volume 2:Functional Materials published by MC Publishing Company and PCTPublication WO 03/024222.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energy millSuspensions are usually prepared by wet-milling; see, for example, U.S.Pat. No. 3,060,084. Granules and pellets can be prepared by spraying theactive material upon preformed granular carriers or by agglomerationtechniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4,1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed.,McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546.Pellets can be prepared as described in U.S. Pat. No. 4,172,714.Water-dispersible and water-soluble granules can be prepared as taughtin U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493.Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat.No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared astaught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-C. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be constructed as merely illustrative, andnot limiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example B

Granule Compound 2 10.0% attapulgite granules (low volatile matter,0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example C

Extruded Pellet Compound 8 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example D

Emulsifiable Concentrate Compound 20 20.0% blend of oil solublesulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%

Example E

Microemulsion Compound 21 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water20.0%

Example F

Seed Treatment Compound 101 20.00% polyvinylpyrrolidone-vinyl acetatecopolymer 5.00% montan acid wax 5.00% calcium ligninsulfonate 1.00%polyoxyethylene/polyoxypropylene block copolymers 1.00% stearyl alcohol(POE 20) 2.00% polyorganosilane 0.20% colorant red dye 0.05% water65.75%

Example G

Fertilizer Stick Compound 201 2.50% pyrrolidone-styrene copolymer 4.80%tristyrylphenyl 16-ethoxylate 2.30% talc 0.80% corn starch 5.00%Nitrophoska ® Permanent 15-9-15 slow-release fertilizer 36.00% (BASF)kaolin 38.00% water 10.60%

Compounds of this invention exhibit activity against a wide spectrum ofinvertebrate pests. These pests include invertebrates inhabiting avariety of environments such as, for example, plant foliage, roots,soil, harvested crops or other foodstuffs, building structures or animalinteguments. These pests include, for example, invertebrates feeding onfoliage (including leaves, stems, flowers and fruits), seeds, wood,textile fibers or animal blood or tissues, and thereby causing injury ordamage to, for example, growing or stored agronomic crops, forests,greenhouse crops, ornamentals, nursery crops, stored foodstuffs or fiberproducts, or houses or other structures or their contents, or beingharmful to animal health or public health. Those skilled in the art willappreciate that not all compounds are equally effective against allgrowth stages of all pests.

These present compounds and compositions are thus useful agronomicallyfor protecting field crops from phytophagous invertebrate pests, andalso nonagronomically for protecting other horticultural crops andplants from phytophagous invertebrate pests. This utility includesprotecting crops and other plants (i.e. both agronomic and nonagronomic)that contain genetic material introduced by genetic engineering (i.e.transgenic) or modified by mutagenesis to provide advantageous traits.Examples of such traits include tolerance to herbicides, resistance tophytophagous pests (e.g., insects, mites, aphids, spiders, nematodes,snails, plant-pathogenic fungi, bacteria and viruses), improved plantgrowth, increased tolerance of adverse growing conditions such as highor low temperatures, low or high soil moisture, and high salinity,increased flowering or fruiting, greater harvest yields, more rapidmaturation, higher quality and/or nutritional value of the harvestedproduct, or improved storage or process properties of the harvestedproducts. Transgenic plants can be modified to express multiple traits.Examples of plants containing traits provided by genetic engineering ormutagenesis include varieties of corn, cotton, soybean and potatoexpressing an insecticidal Bacillus thuringiensis toxin such as YIELDGARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, andherbicide-tolerant varieties of corn, cotton, soybean and rapeseed suchas ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®, as well ascrops expressing N-acetyltransferase (GAT) to provide resistance toglyphosate herbicide, or crops containing the HRA gene providingresistance to herbicides inhibiting acetolactate synthase (ALS). Thepresent compounds and compositions may interact synergistically withtraits introduced by genetic engineering or modified by mutagenesis,thus enhancing phenotypic expression or effectiveness of the traits orincreasing the invertebrate pest control effectiveness of the presentcompounds and compositions. In particular, the present compounds andcompositions may interact synergistically with the phenotypic expressionof proteins or other natural products toxic to invertebrate pests toprovide greater-than-additive control of these pests.

Nonagronomic uses refer to invertebrate pest control in the areas otherthan fields of crop plants. Nonagronomic uses of the present compoundsand compositions include control of invertebrate pests in stored grains,beans and other foodstuffs, and in textiles such as clothing andcarpets. Nonagronomic uses of the present compounds and compositionsalso include invertebrate pest control in ornamental plants, forests, inyards, along roadsides and railroad rights of way, and on turf such aslawns, golf courses and pastures. Nonagronomic uses of the presentcompounds and compositions also include invertebrate pest control inhouses and other buildings which may be occupied by humans and/orcompanion, farm, ranch, zoo or other animals. Nonagronomic uses of thepresent compounds and compositions also include the control of pestssuch as termites that can damage wood or other structural materials usedin buildings.

Nonagronomic uses of the present compounds and compositions also includeprotecting human and animal health by controlling invertebrate peststhat are parasitic or transmit infectious diseases. The controlling ofanimal parasites includes controlling external parasites that areparasitic to the surface of the body of the host animal (e.g.,shoulders, armpits, abdomen, inner part of the thighs) and internalparasites that are parasitic to the inside of the body of the hostanimal (e.g., stomach, intestine, lung, veins, under the skin, lymphatictissue). External parasitic or disease transmitting pests include, forexample, chiggers, ticks, lice, mosquitoes, flies, mites and fleas.Internal parasites include heartworms, hookworms and helminths.Compounds and compositions of the present invention are suitable forsystemic and/or non-systemic control of infestation or infection byparasites on animals. Compounds and compositions of the presentinvention are particularly suitable for combating external parasitic ordisease transmitting pests. Compounds and compositions of the presentinvention are suitable for combating parasites that infest agriculturalworking animals, such as cattle, sheep, goats, horses, pigs, donkeys,camels, buffalos, rabbits, hens, turkeys, ducks, geese and bees; petanimals and domestic animals such as dogs, cats, pet birds and aquariumfish; as well as so-called experimental animals, such as hamsters,guinea pigs, rats and mice. By combating these parasites, fatalities andperformance reduction (in term of meat, milk, wool, skins, eggs, honey,etc.) are reduced, so that applying a composition comprising a compoundof the present invention allows more economic and simple husbandry ofanimals.

Examples of agronomic or nonagronomic invertebrate pests include eggs,larvae and adults of the order Lepidoptera, such as armyworms, cutworms,loopers, and heliothines in the family Noctuidae (e.g., pink stem borer(Sesamia inferens Walker), corn stalk borer (Sesamia nonagrioidesLefebvre), southern armyworm (Spodoptera eridania Cramer), fall armyworm(Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exiguaHübner), cotton leafworm (Spodoptera littoralis Boisduval),yellowstriped armyworm (Spodoptera ornithogalli Guenée), black cutworm(Agrotis ipsilon Hufnagel), velvetbean caterpillar (Anticarsiagemmatalis Hübner), green fruitworm (Lithophane antennata Walker),cabbage armyworm (Barathra brassicae Linnaeus), soybean looper(Pseudoplusia includens Walker), cabbage looper (Trichoplusia niHübner), tobacco budworm (Heliothis virescens Fabricius)); borers,casebearers, webworms, coneworms, cabbageworms and skeletonizers fromthe family Pyralidae (e.g., European corn borer (Ostrinia nubilalisHübner), navel orangeworm (Amyelois transitella Walker), corn rootwebworm (Crambus caliginosellus Clemens), sod webworms (Pyralidae:Crambinae) such as sod worm (Herpetogramma licarsisalis Walker),sugarcane stem borer (Chilo infuscatellus Snellen), tomato small borer(Neoleucinodes elegantalis Guenée), green leafroller (Cnaphalocerusmedinalis), grape leaffolder (Desmia funeralis Hübner), melon worm(Diaphania nitidalis Stoll), cabbage center grub (Helluala hydralisGuenée), yellow stem borer (Scirpophaga incertulas Walker), early shootborer (Scirpophaga infuscatellus Snellen), white stem borer (Scirpophagainnotata Walker), top shoot borer (Scirpophaga nivella Fabricius),dark-headed rice borer (Chilo polychrysus Meyrick), cabbage clustercaterpillar (Crocidolomia binotalis English)); leafrollers, budworms,seed worms, and fruit worms in the family Tortricidae (e.g., codlingmoth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteanaClemens), oriental fruit moth (Grapholita molesta Busck), citrus falsecodling moth (Cryptophlebia leucotreta Meyrick), citrus borer(Ecdytolopha aurantiana Lima), redbanded leafroller (Argyrotaeniavelutinana Walker), obliquebanded leafroller (Choristoneura rosaceanaHarris), light brown apple moth (Epiphyas postvittana Walker), Europeangrape berry moth (Eupoecilia ambiguella Hübner), apple bud moth(Pandemis pyrusana Kearfott), omnivorous leafroller (Platynota stultanaWalsingham), barred fruit-tree tortrix (Pandemis cerasana Hübner), applebrown tortrix (Pandemis heparana Denis & Schiffermüller)); and manyother economically important lepidoptera (e.g., diamondback moth(Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiellaSaunders), gypsy moth (Lymantria dispar Linnaeus), peach fruit borer(Carposina niponensis Walsingham), peach twig borer (Anarsia lineatellaZeller), potato tuberworm (Phthorimaea operculella Zeller), spottedteniform leafminer (Lithocolletis blancardella Fabricius), Asiatic appleleafminer (Lithocolletis ringoniella Matsumura), rice leaffolder(Lerodea eufala Edwards), apple leafminer (Leucoptera scitella Zeller));eggs, nymphs and adults of the order Blattodea including cockroachesfrom the families Blattellidae and Blattidae (e.g., oriental cockroach(Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinaiMizukubo), German cockroach (Blattella germanica Linnaeus), brownbandedcockroach (Supella longipalpa Fabricius), American cockroach(Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunneaBurmeister), Madeira cockroach (Leucophaea maderae Fabricius)), smokybrown cockroach (Periplaneta fuliginosa Service), Australian Cockroach(Periplaneta australasiae Fabr.), lobster cockroach (Nauphoeta cinereaOlivier) and smooth cockroach (Symploce pallens Stephens)); eggs, foliarfeeding, fruit feeding, root feeding, seed feeding and vesicular tissuefeeding larvae and adults of the order Coleoptera including weevils fromthe families Anthribidae, Bruchidae, and Curculionidae (e.g., bollweevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrusoryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus),rice weevil (Sitophilus oryzae Linnaeus)), annual bluegrass weevil(Listronotus maculicollis Dietz), bluegrass billbug (Sphenophorusparvulus Gyllenhal), hunting billbug (Sphenophorus venatus vestitus),Denver billbug (Sphenophorus cicatristriatus Fahraeus)); flea beetles,cucumber beetles, rootworms, leaf beetles, potato beetles, andleafminers in the family Chrysomelidae (e.g., Colorado potato beetle(Leptinotarsa decemlineata Say), western corn rootworm (Diabroticavirgifera virgifera LeConte)); chafers and other beetles from the familyScarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), orientalbeetle (Anomala orientalis Waterhouse, Exomala orientalis (Waterhouse)Baraud), northern masked chafer (Cyclocephala borealis Arrow), southernmasked chafer (Cyclocephala immaculata Olivier or C. lurida Bland) dungbeetle and white grub (Aphodius spp.), black turfgrass ataenius(Ataenius spretulus Haldeman), green June beetle (Cotinis nitidaLinnaeus), Asiatic garden beetle (Maladera castanea Arrow), May/Junebeetles (Phyllophaga spp.) and European chafer (Rhizotrogus majalisRazoumowsky)); carpet beetles from the family Dermestidae; wirewormsfrom the family Elateridae; bark beetles from the family Scolytidae andflour beetles from the family Tenebrionidae. In addition, agronomic andnonagronomic pests include: eggs, adults and larvae of the orderDermaptera including earwigs from the family Forficulidae (e.g.,European earwig (Forficula auricularia Linnaeus), black earwig(Chelisoches mono Fabricius)); eggs, immatures, adults and nymphs of theorders Hemiptera and Homoptera such as, plant bugs from the familyMiridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoascaspp.) from the family Cicadellidae, bed bugs (e.g., Cimex lectulariusLinnaeus) from the family Cimicidae, planthoppers from the familiesFulgoroidae and Delphacidae, treehoppers from the family Membracidae,psyllids from the family Psyllidae, whiteflies from the familyAleyrodidae, aphids from the family Aphididae, phylloxera from thefamily Phylloxeridae, mealybugs from the family Pseudococcidae, scalesfrom the families Coccidae, Diaspididae and Margarodidae, lace bugs fromthe family Tingidae, stink bugs from the family Pentatomidae, chinchbugs (e.g., hairy chinch bug (Blissus leucopterus hirtus Montandon) andsouthern chinch bug (Blissus insularis Barber)) and other seed bugs fromthe family Lygaeidae, spittlebugs from the family Cercopidae squash bugsfrom the family Coreidae, and red bugs and cotton stainers from thefamily Pyrrhocoridae. Also included are eggs, larvae, nymphs and adultsof the order Acari (mites) such as spider mites and red mites in thefamily Tetranychidae (e.g., European red mite (Panonychus ulmi Koch),two spotted spider mite (Tetranychus urticae Koch), McDaniel mite(Tetranychus mcdanieli McGregor)); flat mites in the familyTenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor));rust and bud mites in the family Eriophyidae and other foliar feedingmites and mites important in human and animal health, i.e. dust mites inthe family Epidermoptidae, follicle mites in the family Demodicidae,grain mites in the family Glycyphagidae, ticks in the order Ixodidae(e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick(Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilisSay), lone star tick (Amblyomma americanum Linnaeus)) and scab and itchmites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; eggs,adults and immatures of the order Orthoptera including grasshoppers,locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplussanguinipes Fabricius, M. differentialis Thomas), American grasshoppers(e.g., Schistocerca americana Drury), desert locust (Schistocercagregaria Forskal), migratory locust (Locusta migratoria Linnaeus), bushlocust (Zonocerus spp.), house cricket (Acheta domesticus Linnaeus),mole crickets (e.g., tawny mole cricket (Scapteriscus vicinus Scudder)and southern mole cricket (Scapteriscus borellii Giglio-Tos)); eggs,adults and immatures of the order Diptera including leafminers (e.g.,Liriomyza spp. such as serpentine vegetable leafminer (Liriomyza sativaeBlanchard)), midges, fruit flies (Tephritidae), frit flies (e.g.,Oscinella frit Linnaeus), soil maggots, house flies (e.g., Muscadomestica Linnaeus), lesser house flies (e.g., Fannia canicularisLinnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitransLinnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp.,Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanusspp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs(e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g.,Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g.,Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimuliumspp., Simulium spp.), biting midges, sand flies, sciarids, and otherNematocera; eggs, adults and immatures of the order Thysanopteraincluding onion thrips (Thrips tabaci Lindeman), flower thrips(Frankliniella spp.), and other foliar feeding thrips; insect pests ofthe order Hymenoptera including ants of the Family Formicidae includingthe Florida carpenter ant (Camponotus floridanus Buckley), red carpenterant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotuspennsylvanicus De Geer), white-footed ant (Technomyrmex albipes fr.Smith), big headed ants (Pheidole sp.), ghost ant (Tapinomamelanocephalum Fabricius); Pharaoh ant (Monomorium pharaonis Linnaeus),little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsisgeminata Fabricius), red imported fire ant (Solenopsis invicta Buren),Argentine ant (Iridomyrmex humilis Mayr), crazy ant (Paratrechinalongicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus),cornfield ant (Lasius alienus Forster) and odorous house ant (Tapinomasessile Say). Other Hymenoptera including bees (including carpenterbees), hornets, yellow jackets, wasps, and sawflies (Neodiprion spp.;Cephus spp.); insect pests of the order Isoptera including termites inthe Termitidae (e.g., Macrotermes sp., Odontotermes obesus Rambur),Kalotermitidae (e.g., Cryptotermes sp.), and Rhinotermitidae (e.g.,Reticulitermes sp., Coptotermes sp., Heterotermes tenuis Hagen)families, the eastern subterranean termite (Reticulitermes flavipesKollar), western subterranean termite (Reticulitermes hesperus Banks),Formosan subterranean termite (Coptotermes formosanus Shiraki), WestIndian drywood termite (Incisitermes immigrans Snyder), powder posttermite (Cryptotermes brevis Walker), drywood termite (Incisitermessnyderi Light), southeastern subterranean termite (Reticulitermesvirginicus Banks), western drywood termite (Incisitermes minor Hagen),arboreal termites such as Nasutitermes sp. and other termites ofeconomic importance; insect pests of the order Thysanura such assilverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobiadomestica Packard); insect pests of the order Mallophaga and includingthe head louse (Pediculus humanus capitis De Geer), body louse(Pediculus humanus Linnaeus), chicken body louse (Menacanthus stramineusNitszch), dog biting louse (Trichodectes canis De Geer), fluff louse(Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank),short-nosed cattle louse (Haematopinus eurysternus Nitzsch), long-nosedcattle louse (Linognathus vituli Linnaeus) and other sucking and chewingparasitic lice that attack man and animals; insect pests of the orderSiphonoptera including the oriental rat flea (Xenopsylla cheopisRothschild), cat flea (Ctenocephalides felis Bouche), dog flea(Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinaeSchrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea(Pulex irritans Linnaeus) and other fleas afflicting mammals and birds.Additional arthropod pests covered include: spiders in the order Araneaesuch as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik)and the black widow spider (Latrodectus mactans Fabricius), andcentipedes in the order Scutigeromorpha such as the house centipede(Scutigera coleoptrata Linnaeus). Compounds of the present inventionalso have activity on members of the Classes Nematoda, Cestoda,Trematoda, and Acanthocephala including economically important membersof the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida,and Enoplida such as but not limited to economically importantagricultural pests (i.e. root knot nematodes in the genus Meloidogyne,lesion nematodes in the genus Pratylenchus, stubby root nematodes in thegenus Trichodorus, etc.) and animal and human health pests (i.e. alleconomically important flukes, tapeworms, and roundworms, such asStrongylus vulgaris in horses, Toxocara canis in dogs, Haemonchuscontortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephalaperfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

Compounds of the invention show particularly high activity against pestsin the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit tree leaf roller), A. rosanaLinnaeus (European leaf roller) and other Archips species, Chilosuppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee(rice leaf roller), Crambus caliginosellus Clemens (corn root webworm),Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonellaLinnaeus (codling moth), Earias insulana Boisduval (spiny bollworm),Earias vittella Fabricius (spotted bollworm), Helicoverpa armigeraHübner (American bollworm), Helicoverpa zea Boddie (corn earworm),Heliothis virescens Fabricius (tobacco budworm), Herpetogrammalicarsisalis Walker (sod webworm), Lobesia botrana Denis &Schiffermüller (grape berry moth), Pectinophora gossypiella Saunders(pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer),Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus(small white butterfly), Plutella xylostella Linnaeus (diamondbackmoth), Spodoptera exigua Hübner (beet armyworm), Spodoptera lituraFabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperdaJ. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) andTuta absoluta Meyrick (tomato leafminer)).

Compounds of the invention also have significant activity on membersfrom the order Homoptera including: Acyrthisiphon pisum Harris (peaaphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (blackbean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphispomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid),Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefoliiCockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko(Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy appleaphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopteruspruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnipaphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipumeuphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potatoaphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid),Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch(corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid),Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius(English grain aphid), Therioaphis maculata Buckton (spotted alfalfaaphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid),and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp.(adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisiatabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisiaargentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citriAshmead (citrus whitefly) and Trialeurodes vaporariorum Westwood(greenhouse whitefly); Empoasca fabae Harris (potato leafhopper),Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestesquadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler(green leafhopper), Nephotettix nigropictus Stål (rice leafhopper),Nilaparvata lugens Stål (brown planthopper), Peregrinus maidis Ashmead(corn planthopper), Sogatella furcifera Horvath (white-backedplanthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocybapomaria McAtee white apple leafhopper, Erythroneoura spp. (grapeleafhoppers); Magicidada septendecim Linnaeus (periodical cicada);Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotusperniciosus Comstock (San Jose scale); Planococcus citri Risso (citrusmealybug); Pseudococcus spp. (other mealybug complex); Cacopsyllapyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmonpsylla).

Compounds of this invention also have activity on members from the orderHemiptera including: Acrosternum hilare Say (green stink bug), Anasatristis De Geer (squash bug), Blissus leucopterus leucopterus Say(chinch bug), Cimex lectularius Linnaeus (bed bug) Corythuca gossypiiFabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug),Dysdercus suturellus Henich-Schäffer (cotton stainer), Euchistus servusSay (brown stink bug), Euchistus variolarius Palisot de Beauvois(one-spotted stink bug), Graptosthetus spp. (complex of seed bugs),Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolarisPalisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus(southern green stink bug), Oebalus pugnax Fabricius (rice stink bug),Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelisseriatus Reuter (cotton fleahopper). Other insect orders controlled bycompounds of the invention include Thysanoptera (e.g., Frankliniellaoccidentalis Pergande (western flower thrip), Scirthothrips citriMoulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip),and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera(e.g., Leptinotarsa decemlineata Say (Colorado potato beetle), Epilachnavarivestis Mulsant (Mexican bean beetle) and wireworms of the generaAgriotes, Athous or Limonius).

Note that some contemporary classification systems place Homoptera as asuborder within the order Hemiptera.

Of note is use of compounds of this invention for controlling silverleafwhitefly (Bemisia argentifolii). Of note is use of compounds of thisinvention for controlling western flower thrip (Frankliniellaoccidentalis). Of note is use of compounds of this invention forcontrolling potato leafhopper (Empoasca fabae). Of note is use ofcompounds of this invention for controlling corn planthopper (Peregrinusmaidis). Of note is use of compounds of this invention for controllingcotton melon aphid (Aphis gossypii). Of note is use of compounds of thisinvention for controlling green peach aphid (Myzus persicae). Of note isuse of compounds of this invention for controlling diamondback moth(Plutella xylostella). Of note is use of compounds of this invention forcontrolling fall armyworm (Spodoptera frugiperda).

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including insecticides,fungicides, nematicides, bactericides, acaricides, herbicides, growthregulators such as rooting stimulants, chemosterilants, semiochemicals,repellents, attractants, pheromones, feeding stimulants, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agronomic and nonagronomic utility. Thus the presentinvention also pertains to a composition comprising a biologicallyeffective amount of a compound of Formula 1, an N-oxide or salt thereof,and an effective amount of at least one additional biologically activecompound or agent and can further comprise at least one of a surfactant,a solid diluent or a liquid diluent. The other biologically activecompounds or agents can be formulated in compositions comprising atleast one of a surfactant, solid or liquid diluent. For mixtures of thepresent invention, the other biologically active compounds or agents canbe formulated together with the present compounds, including thecompounds of Formula 1, to form a premix, or the other biologicallyactive compounds or agents can be formulated separately from the presentcompounds, including the compounds of Formula 1, and the twoformulations combined together before application (e.g., in a spraytank) or, alternatively, applied in succession.

Other biologically active compounds or agents useful in the compositionsof the present invention can be selected from invertebrate pest controlagents having a different mode of action or a different chemical classsodium channel modulators, cholinesterase inhibitors, neonicotinoids,insecticidal macrocyclic lactones, GABA (γ-aminobutyric acid)-regulatedchloride channel blockers, chitin synthesis inhibitors, juvenile hormonemimics, octopamine receptor ligands, ecdysone agonists, ryanodinereceptor ligands, nereistoxin analogs, mitochondrial electron transportinhibitors, lipid biosynthesis inhibitors, cyclodiene insecticides,molting inhibitors and biological agents including nucleopolyhedrovirus(NPV), a member of Bacillus thuringiensis, an encapsulateddelta-endotoxin of Bacillus thuringiensis and a naturally occurring or agenetically modified viral insecticide.

Of note is a composition of the present invention wherein at least oneadditional biologically active compound or agent is selected frominsecticides of the group consisting of sodium channel modulators,cholinesterase inhibitors, neonicotinoids, insecticidal macrocycliclactones, GABA-regulated chloride channel blockers, chitin synthesisinhibitors, juvenile hormone mimics, octopamine receptor ligands,ecdysone agonists, ryanodine receptor ligands, nereistoxin analogs,mitochondrial electron transport inhibitors, lipid biosynthesisinhibitors, cyclodiene insecticides, molting inhibitors and biologicalagents including nucleopolyhedrovirus, a member of Bacillusthuringiensis, an encapsulated delta-endotoxin of Bacillus thuringiensisand a naturally occurring or a genetically modified viral insecticide.

Of particular note are additional biologically active compounds oragents selected from insecticides of the group consisting of sodiumchannel modulators, cholinesterase inhibitors, neonicotinoids,insecticidal macrocyclic lactones, GABA-regulated chloride channelblockers, chitin synthesis inhibitors, juvenile hormone mimics,octopamine receptor ligands, ecdysone agonists, ryanodine receptorligands, nereistoxin analogs, mitochondrial electron transportinhibitors, lipid biosynthesis inhibitors, cyclodiene insecticides,nucleopolyhedrovirus; a member of Bacillus thuringiensis, anencapsulated delta-endotoxin of Bacillus thuringiensis; and a naturallyoccurring or a genetically modified viral insecticide.

Of further note are additional biologically active compounds or agentsselected from insecticides of the group consisting of pyrethroids,carbamates, neonicotinoids, neuronal sodium channel blockers,insecticidal macrocyclic lactones, γ-aminobutyric acid antagonists,insecticidal ureas and juvenile hormone mimics, a member of Bacillusthuringiensis, a Bacillus thuringiensis delta-endotoxin, and a naturallyoccurring or a genetically modified viral insecticide.

Examples of such biologically active compounds or agents with whichcompounds of this invention can be formulated are: insecticides such asabamectin, acephate, acetamiprid, acetoprole, amidoflumet (S-1955),avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate,buprofezin, bistrifluoron, buprofezin, carbofuran, cartap, chlorfenapyr,chlorfluazuron, chlorantraniliprole (DPX-E2Y45), chlorpyrifos,chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen,cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrinlambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin,dimethoate, dinotefuran, diofenolan, emamectin, endosulfan,esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin,fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate,tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos,halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,metofluthrin, monocrotophos, methoxyfenozide, monocrotophos, nitenpyram,nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion,parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,pirimicarb, profenofos, profluthrin, protrifenbute, pymetrozine,pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole,pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen,spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide,teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin,triazamate, trichlorfon and triflumuron; fungicides such as acibenzolar,aldimorph, amisulbrom, azaconazole, azoxystrobin, benalaxyl, benomyl,benthiavalicarb, benthiavalicarb-isopropyl, binomial, biphenyl,bitertanol, blasticidin-S, Bordeaux mixture (Tribasic copper sulfate),boscalid/nicobifen, bromuconazole, bupirimate, buthiobate, carboxin,carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil,chlozolinate, clotrimazole, copper oxychloride, copper salts such ascopper sulfate and copper hydroxide, cyazofamid, cyflunamid, cymoxanil,cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine,dicloran, diethofencarb, difenoconazole, dimethomorph, dimoxystrobin,diniconazole, diniconazole-M, dinocap, discostrobin, dithianon,dodemorph, dodine, econazole, etaconazole, edifenphos, epoxiconazole,ethaboxam, ethirimol, ethridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid, fenfuram, fenhexamide, fenoxanil,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferfurazoate, ferimzone, fluazinam, fludioxonil,flumetover, fluopicolide, fluoxastrobin, fluquinconazole,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol,folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametapyr,hexaconazole, hymexazole, guazatine, imazalil, imibenconazole,iminoctadine, iodicarb, ipconazole, iprobenfos, iprodione, iprovalicarb,isoconazole, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb,mandipropamid, maneb, mapanipyrin, mefenoxam, mepronil, metalaxyl,metconazole, methasulfocarb, metiram, metominostrobin/fenominostrobin,mepanipyrim, metrafenone, miconazole, myclobutanil, neo-asozin (ferricmethanearsonate), nuarimol, octhilinone, ofurace, orysastrobin,oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, paclobutrazol,penconazole, pencycuron, penthiopyrad, perfurazoate, phosphonic acid,phthalide, picobenzamid, picoxystrobin, polyoxin, probenazole,prochloraz, procymidone, propamocarb, propamocarb-hydrochloride,propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin,pryazophos, pyrifenox, pyrimethanil, pyrifenox, pyroInitrine,pyroquilon, quinconazole, quinoxyfen, quintozene, silthiofam,simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole,techrazene, tecloftalam, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil,tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, triarimol,triazoxide, tridemorph, trimoprhamide tricyclazole, trifloxystrobin,triforine, triticonazole, uniconazole, validamycin, vinclozolin, zineb,ziram, and zoxamide; nematicides such as aldicarb, imicyafos, oxamyl andfenamiphos; bactericides such as streptomycin; acaricides such asamitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; andbiological agents including entomopathogenic bacteria, such as Bacillusthuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki,and the encapsulated delta-endotoxins of Bacillus thuringiensis (e.g.,Cellcap, MPV, MPVII); entomopathogenic fungi, such as green muscardinefungus; and entomopathogenic virus including baculovirus,nucleopolyhedrovirus (NPV) such as Helicoverpa zea nucleopolyhedrovirus(HzNPV), Anagrapha falcifera nucleopolyhedrovirus (AfNPV); andgranulosis virus (GV) such as Cydia pomonella granulosis virus (CpGV).

Compounds of this invention and compositions thereof can be applied toplants genetically transformed to express proteins toxic to invertebratepests (such as Bacillus thuringiensis delta-endotoxins). The effect ofthe exogenously applied invertebrate pest control compounds of thisinvention may be synergistic with the expressed toxin proteins.

General references for these agricultural protectants (i.e.insecticides, fungicides, nematicides, acaricides, herbicides andbiological agents) include The Pesticide Manual, 13th Edition, C. D. S.Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K.,2003 and The BioPesticide Manual, 2^(nd) Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2001.

Of note is a composition of the present invention wherein at least oneadditional biologically active compound or agent is selected from thegroup consisting of abamectin, acephate, acetamiprid, acetoprole,aldicarb, amidoflumet, amitraz, avermectin, azadirachtin,azinphos-methyl, bifenthrin, bifenazate, bistrifluoron, buprofezin,carbofuran, cartap, chinomethionat, chlorfenapyr, chlorfluazuron,chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, chlorobenzilate,chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin,cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cyhexatin,cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon,dicofol, dieldrin, dienochlor, diflubenzuron, dimefluthrin, dimethoate,dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate,ethiprole, etoxazole, fenamiphos, fenazaquin, fenbutatin oxide,fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenvalerate,fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate,flufenerim, flufenoxuron, fonophos, halofenozide, hexaflumuron,hexythiazox, hydramethylnon, imicyafos, imidacloprid, indoxacarb,isofenphos, lufenuron, malathion, metaflumizone, metaldehyde,methamidophos, methidathion, methomyl, methoprene, methoxychlor,methoxyfenozide, metofluthrin, monocrotophos, nitenpyram, nithiazine,novaluron, noviflumuron, oxamyl, parathion, parathion-methyl,permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb,profenofos, profluthrin, propargite, protrifenbute, pymetrozine,pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon,pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad,spiridiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide,tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad,tralomethrin, triazamate, trichlorfon, triflumuron, Bacillusthuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki,nucleopolyhedrovirus, an encapsulated delta-endotoxin of Bacillusthuringiensis, baculovirus, entomopathogenic bacteria, entomopathogenicvirus and entomopathogenic fungi.

Also of note is a composition of the present invention wherein at leastone additional biologically active compound or agent is selected fromthe group consisting of abamectin, acetamiprid, amitraz, avermectin,azadirachtin, bifenthrin, buprofezin, cartap, chlorantraniliprole,chlorfenapyr, chlorpyrifos, clothianidin, cyfluthrin, beta-cyfluthrin,cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate,ethiprole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid,flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, imidacloprid,indoxacarb, lufenuron, metaflumizone, methomyl, methoprene,methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine,pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram,spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus and an encapsulateddelta-endotoxin of Bacillus thuringiensis.

For embodiments where one or more of these various mixing partners areused, the weight ratio of these various mixing partners (in total) tothe compound of Formula 1 is typically between about 1:3000 and about3000:1. Of note are weight ratios between about 1:300 and about 300:1(for example ratios between about 1:30 and about 30:1). One skilled inthe art can easily determine through simple experimentation thebiologically effective amounts of active ingredients necessary for thedesired spectrum of biological activity. It will be evident thatincluding these additional components may expand the spectrum ofinvertebrate pests controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly invertebrate pest control)compounds or agents (i.e. active ingredients) can result in agreater-than-additive (i.e. synergistic) effect. Reducing the quantityof active ingredients released in the environment while ensuringeffective pest control is always desirable. When synergism ofinvertebrate pest control active ingredients occurs at application ratesgiving agronomically satisfactory levels of invertebrate pest control,such combinations can be advantageous for reducing crop production costand decreasing environmental load.

Of note is a combination of a compound of Formula 1 with at least oneother invertebrate pest control active ingredient. Of particular note issuch a combination where the other invertebrate pest control activeingredient has different site of action from the compound of Formula 1.In certain instances, a combination with at least one other invertebratepest control active ingredient having a similar spectrum of control buta different site of action will be particularly advantageous forresistance management. Thus, a composition of the present invention canfurther comprise a biologically effective amount of at least oneadditional invertebrate pest control active ingredient having a similarspectrum of control but a different site of action. Contacting a plantgenetically modified to express an invertebrate pest compound (e.g.,protein) or the locus of the plant with a biologically effective amountof a compound of this invention can also provide a broader spectrum ofplant protection and be advantageous for resistance management.

Table A lists specific combinations of a compound of Formula 1 withother invertebrate pest control agents illustrative of the mixtures,compositions and methods of the present invention. The first column ofTable A lists the specific invertebrate pest control agents (e.g.,“Abamectin” in the first line). The second column of Table A lists themode of action (if known) or chemical class of the invertebrate pestcontrol agents. The third column of Table A lists embodiment(s) ofranges of weight ratios for rates at which the invertebrate pest controlagent can be applied relative to a compound of Formula 1, an N-oxide, ora salt thereof, (e.g., “50:1 to 1:50” of abamectin relative to acompound of Formula 1 by weight). Thus, for example, the first line ofTable A specifically discloses the combination of a compound of Formula1 with abamectin can be applied in a weight ratio between 50:1 to 1:50.The remaining lines of Table A are to be construed similarly. Of furthernote Table A lists specific combinations of a compound of Formula 1 withother invertebrate pest control agents illustrative of the mixtures,compositions and methods of the present invention and includesadditional embodiments of weight ratio ranges for application rates.

TABLE A Invertebrate Pest Mode of Action or Typical Control AgentChemical Class Weight Ratio Abamectin macrocyclic lactones 50:1 to 1:50Acetamiprid neonicotinoids 150:1 to 1:200 Amitraz octopamine receptorligands 200:1 to 1:100 Avermectin macrocyclic lactones 50:1 to 1:50Azadirachtin ecdysone agonists 100:1 to 1:120 Beta-cyfluthrin sodiumchannel modulators 150:1 to 1:200 Bifenthrin sodium channel modulators100:1 to 1:10  Buprofezin chitin synthesis inhibitors 500:1 to 1:50 Cartap nereistoxin analogs 100:1 to 1:200 Chlorantraniliprole ryanodinereceptor ligands 100:1 to 1:120 Chlorfenapyr mitochondrial electron300:1 to 1:200 transport inhibitors Chlorpyrifos cholinesteraseinhibitors 500:1 to 1:200 Clothianidin neonicotinoids 100:1 to 1:400Cyfluthrin sodium channel modulators 150:1 to 1:200 Cyhalothrin sodiumchannel modulators 150:1 to 1:200 Cypermethrin sodium channel modulators150:1 to 1:200 Cyromazine chitin synthesis inhibitors 400:1 to 1:50 Deltamethrin sodium channel modulators  50:1 to 1:400 Dieldrincyclodiene insecticides 200:1 to 1:100 Dinotefuran neonicotinoids 150:1to 1:200 Diofenolan molting inhibitor 150:1 to 1:200 Emamectinmacrocyclic lactones 50:1 to 1:10 Endosulfan cyclodiene insecticides200:1 to 1:100 Esfenvalerate sodium channel modulators 100:1 to 1:400Ethiprole GABA-regulated chloride 200:1 to 1:100 channel blockersFenothiocarb 150:1 to 1:200 Fenoxycarb juvenile hormone mimics 500:1 to1:100 Fenvalerate sodium channel modulators 150:1 to 1:200 FipronilGABA-regulated chloride 150:1 to 1:100 channel blockers Flonicamid 200:1to 1:100 Flubendiamide ryanodine receptor ligands 100:1 to 1:120Flufenoxuron chitin synthesis inhibitors 200:1 to 1:100 Hexaflumuronchitin synthesis inhibitors 300:1 to 1:50  Hydramethylnon mitochondrialelectron 150:1 to 1:250 transport inhibitors Imidacloprid neonicotinoids1000:1 to 1:1000 Indoxacarb sodium channel modulators 200:1 to 1:50 Lambda-cyhalothrin sodium channel modulators  50:1 to 1:250 Lufenuronchitin synthesis inhibitors 500:1 to 1:250 Metaflumizone 200:1 to 1:200Methomyl cholinesterase inhibitors 500:1 to 1:100 Methoprene juvenilehormone mimics 500:1 to 1:100 Methoxyfenozide ecdysone agonists 50:1 to1:50 Nitenpyram neonicotinoids 150:1 to 1:200 Nithiazine neonicotinoids150:1 to 1:200 Novaluron chitin synthesis inhibitors 500:1 to 1:150Oxamyl cholinesterase inhibitors 200:1 to 1:200 Pymetrozine 200:1 to1:100 Pyrethrin sodium channel modulators 100:1 to 1:10  Pyridabenmitochondrial electron 200:1 to 1:100 transport inhibitors Pyridalyl200:1 to 1:100 Pyriproxyfen juvenile hormone mimics 500:1 to 1:100Ryanodine ryanodine receptor ligands 100:1 to 1:120 Spinetorammacrocyclic lactones 150:1 to 1:100 Spinosad macrocyclic lactones 500:1to 1:10  Spirodiclofen lipid biosynthesis inhibitors 200:1 to 1:200Spiromesifen lipid biosynthesis inhibitors 200:1 to 1:200 Tebufenozideecdysone agonists 500:1 to 1:250 Thiacloprid neonicotinoids 100:1 to1:200 Thiamethoxam neonicotinoids 1250:1 to 1:1000 Thiodicarbcholinesterase inhibitors 500:1 to 1:400 Thiosultap-sodium 150:1 to1:100 Tralomethrin sodium channel modulators 150:1 to 1:200 Triazamatecholinesterase inhibitors 250:1 to 1:100 Triflumuron chitin synthesisinhibitors 200:1 to 1:100 Bacillus thuringiensis biological agents 50:1to 1:10 Bacillus thuringiensis biological agents 50:1 to 1:10delta-endotoxin NPV (e.g., Gemstar) biological agents 50:1 to 1:10

One embodiment of invertebrate pest control agents (e.g., insecticidesand acaricides) for mixing with compounds of this invention includesodium channel modulators such as bifenthrin, cypermethrin, cyhalothrin,lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, deltamethrin,dimefluthrin, esfenvalerate, fenvalerate, indoxacarb, metofluthrin,profluthrin, pyrethrin and tralomethrin; cholinesterase inhibitors suchas chlorpyrifos, methomyl, oxamyl, thiodicarb and triazamate;neonicotinoids such as acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, nithiazine, thiacloprid and thiamethoxam;insecticidal macrocyclic lactones such as spinetoram, spinosad,abamectin, avermectin and emamectin; GABA (γ-aminobutyricacid)-regulated chloride channel blockers such as endosulfan, ethiproleand fipronil; chitin synthesis inhibitors such as buprofezin,cyromazine, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron and triflumuron; juvenile hormone mimics such asdiofenolan, fenoxycarb, methoprene and pyriproxyfen; octopamine receptorligands such as amitraz; ecdysone agonists such as azadirachtin,methoxyfenozide and tebufenozide; ryanodine receptor ligands such asryanodine, anthranilic diamides such as chlorantraniliprole (see U.S.Pat. No. 6,747,047, PCT Publications WO 2003/015518 and WO 2004/067528)and flubendiamide (see U.S. Pat. No. 6,603,044); nereistoxin analogssuch as cartap; mitochondrial electron transport inhibitors such aschlorfenapyr, hydramethylnon and pyridaben; lipid biosynthesisinhibitors such as spirodiclofen and spiromesifen; cyclodieneinsecticides such as dieldrin; cyflumetofen; fenothiocarb; flonicamid;metaflumizone; pyrafluprole; pyridalyl; pyriprole; pymetrozine;spirotetramat; and thiosultap-sodium. One embodiment of biologicalagents for mixing with compounds of this invention includenucleopolyhedrovirus such as HzNPV and AfNPV; Bacillus thuringiensis andencapsulated delta-endotoxins of Bacillus thuringiensis such as Cellcap,MPV and MPVII; as well as naturally occurring and genetically modifiedviral insecticides including members of the family Baculoviridae as wellas entomophagous fungi. Of note is the composition of the presentinvention wherein the at least one additional biologically activecompound or agent is selected from the Invertebrate Pest Control Agentslisted in Table A above. Also of note is the composition of the presentinvention wherein the at least one additional biologically activecompound or agent is selected from the group consisting of cypermethrin,cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate,tralomethrin, fenothiocarb, methomyl, oxamyl, thiodicarb, acetamiprid,clothianidin, imidacloprid, thiamethoxam, thiacloprid, indoxacarb,spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole,fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen,pymetrozine, amitraz, Bacillus thuringiensis aisawai, Bacillusthuringiensis kurstaki, Bacillus thuringiensis delta endotoxin andentomophagous fungi.

The weight ratios of a compound, including a compound of Formula 1, anN-oxide or a salt thereof, to the additional invertebrate pest controlagent typically are between 1000:1 and 1:1000, with one embodiment beingbetween 500:1 and 1:500, another embodiment being between 250:1 and1:200 and another embodiment being between 100:1 and 1:50.

Listed below in Table B are embodiments of specific compositionscomprising a compound of Formula 1 (compound numbers refer to compoundsin Index Tables A-C) and an additional invertebrate pest control agent.

TABLE B Mixture Comp. Invertebrate Pest No. No. and Control Agent A-1 1and Abamectin A-2 1 and Acetamiprid A-3 1 and Amitraz A-4 1 andAvermectin A-5 1 and Azadirachtin A-6 1 and Beta-cyfluthrin A-7 1 andBifenthrin A-8 1 and Buprofezin A-9 1 and Cartap A-10 1 andChlorantraniliprole A-11 1 and Chlorfenapyr A-12 1 and Chlorpyrifos A-131 and Clothianidin A-14 1 and Cyfluthrin A-15 1 and Cyhalothrin A-16 1and Cypermethrin A-17 1 and Cyromazine A-18 1 and Deltamethrin A-19 1and Dieldrin A-20 1 and Dinotefuran A-21 1 and Diofenolan A-22 1 andEmamectin A-23 1 and Endosulfan A-24 1 and Esfenvalerate A-25 1 andEthiprole A-26 1 and Fenothiocarb A-27 1 and Fenoxycarb A-28 1 andFenvalerate A-29 1 and Fipronil A-30 1 and Flonicamid A-31 1 andFlubendiamide A-32 1 and Flufenoxuron A-33 1 and Hexaflumuron A-34 1 andHydramethylnon A-35 1 and Imidacloprid A-36 1 and Indoxacarb A-37 1 andLambda-cyhalothrin A-38 1 and Lufenuron A-39 1 and Metaflumizone A-40 1and Methomyl A-41 1 and Methoprene A-42 1 and Methoxyfenozide A-43 1 andNitenpyram A-44 1 and Nithiazine A-45 1 and Novaluron A-46 1 and OxamylA-47 1 and Pymetrozine A-48 1 and Pyrethrin A-49 1 and Pyridaben A-50 1and Pyridalyl A-51 1 and Pyriproxyfen A-52 1 and Ryanodine A-53 1 andSpinetoram A-54 1 and Spinosad A-55 1 and Spirodiclofen A-56 1 andSpiromesifen A-57 1 and Tebufenozide A-58 1 and Thiacloprid A-59 1 andThiamethoxam A-60 1 and Thiodicarb A-61 1 and Thiosultap-sodium A-62 1and Tralomethrin A-63 1 and Triazamate A-64 1 and Triflumuron A-65 1 andBacillus thuringiensis A-66 1 and Bacillus thuringiensis delta-endotoxinA-67 1 and NPV (e.g., Gemstar) B-1 2 and Abamectin B-2 2 and AcetamipridB-3 2 and Amitraz B-4 2 and Avermectin B-5 2 and Azadirachtin B-6 2 andBeta-cyfluthrin B-7 2 and Bifenthrin B-8 2 and Buprofezin B-9 2 andCartap B-10 2 and Chlorantraniliprole B-11 2 and Chlorfenapyr B-12 2 andChlorpyrifos B-13 2 and Clothianidin B-14 2 and Cyfluthrin B-15 2 andCyhalothrin B-16 2 and Cypermethrin B-17 2 and Cyromazine B-18 2 andDeltamethrin B-19 2 and Dieldrin B-20 2 and Dinotefuran B-21 2 andDiofenolan B-22 2 and Emamectin B-23 2 and Endosulfan B-24 2 andEsfenvalerate B-25 2 and Ethiprole B-26 2 and Fenothiocarb B-27 2 andFenoxycarb B-28 2 and Fenvalerate B-29 2 and Fipronil B-30 2 andFlonicamid B-31 2 and Flubendiamide B-32 2 and Flufenoxuron B-33 2 andHexaflumuron B-34 2 and Hydramethylnon B-35 2 and Imidacloprid B-36 2and Indoxacarb B-37 2 and Lambda-cyhalothrin B-38 2 and Lufenuron B-39 2and Metaflumizone B-40 2 and Methomyl B-41 2 and Methoprene B-42 2 andMethoxyfenozide B-43 2 and Nitenpyram B-44 2 and Nithiazine B-45 2 andNovaluron B-46 2 and Oxamyl B-47 2 and Pymetrozine B-48 2 and PyrethrinB-49 2 and Pyridaben B-50 2 and Pyridalyl B-51 2 and Pyriproxyfen B-52 2and Ryanodine B-53 2 and Spinetoram B-54 2 and Spinosad B-55 2 andSpirodiclofen B-56 2 and Spiromesifen B-57 2 and Tebufenozide B-58 2 andThiacloprid B-59 2 and Thiamethoxam B-60 2 and Thiodicarb B-61 2 andThiosultap-sodium B-62 2 and Tralomethrin B-63 2 and Triazamate B-64 2and Triflumuron B-65 2 and Bacillus thuringiensis B-66 2 and Bacillusthuringiensis delta-endotoxin B-67 2 and NPV (e.g., Gemstar) C-1 101 andAbamectin C-2 101 and Acetamiprid C-3 101 and Amitraz C-4 101 andAvermectin C-5 101 and Azadirachtin C-6 101 and Beta-cyfluthrin C-7 101and Bifenthrin C-8 101 and Buprofezin C-9 101 and Cartap C-10 101 andChlorantraniliprole C-11 101 and Chlorfenapyr C-12 101 and ChlorpyrifosC-13 101 and Clothianidin C-14 101 and Cyfluthrin C-15 101 andCyhalothrin C-16 101 and Cypermethrin C-17 101 and Cyromazine C-18 101and Deltamethrin C-19 101 and Dieldrin C-20 101 and Dinotefuran C-21 101and Diofenolan C-22 101 and Emamectin C-23 101 and Endosulfan C-24 101and Esfenvalerate C-25 101 and Ethiprole C-26 101 and Fenothiocarb C-27101 and Fenoxycarb C-28 101 and Fenvalerate C-29 101 and Fipronil C-30101 and Flonicamid C-31 101 and Flubendiamide C-32 101 and FlufenoxuronC-33 101 and Hexaflumuron C-34 101 and Hydramethylnon C-35 101 andImidacloprid C-36 101 and Indoxacarb C-37 101 and Lambda-cyhalothrinC-38 101 and Lufenuron C-39 101 and Metaflumizone C-40 101 and MethomylC-41 101 and Methoprene C-42 101 and Methoxyfenozide C-43 101 andNitenpyram C-44 101 and Nithiazine C-45 101 and Novaluron C-46 101 andOxamyl C-47 101 and Pymetrozine C-48 101 and Pyrethrin C-49 101 andPyridaben C-50 101 and Pyridalyl C-51 101 and Pyriproxyfen C-52 101 andRyanodine C-53 101 and Spinetoram C-54 101 and Spinosad C-55 101 andSpirodiclofen C-56 101 and Spiromesifen C-57 101 and Tebufenozide C-58101 and Thiacloprid C-59 101 and Thiamethoxam C-60 101 and ThiodicarbC-61 101 and Thiosultap-sodium C-62 101 and Tralomethrin C-63 101 andTriazamate C-64 101 and Triflumuron C-65 101 and Bacillus thuringiensisC-66 101 and Bacillus thuringiensis delta-endotoxin C-67 101 and NPV(e.g., Gemstar) D-1 104 and Abamectin D-2 104 and Acetamiprid D-3 104and Amitraz D-4 104 and Avermectin D-5 104 and Azadirachtin D-6 104 andBeta-cyfluthrin D-7 104 and Bifenthrin D-8 104 and Buprofezin D-9 104and Cartap D-10 104 and Chlorantraniliprole D-11 104 and ChlorfenapyrD-12 104 and Chlorpyrifos D-13 104 and Clothianidin D-14 104 andCyfluthrin D-15 104 and Cyhalothrin D-16 104 and Cypermethrin D-17 104and Cyromazine D-18 104 and Deltamethrin D-19 104 and Dieldrin D-20 104and Dinotefuran D-21 104 and Diofenolan D-22 104 and Emamectin D-23 104and Endosulfan D-24 104 and Esfenvalerate D-25 104 and Ethiprole D-26104 and Fenothiocarb D-27 104 and Fenoxycarb D-28 104 and FenvalerateD-29 104 and Fipronil D-30 104 and Flonicamid D-31 104 and FlubendiamideD-32 104 and Flufenoxuron D-33 104 and Hexaflumuron D-34 104 andHydramethylnon D-35 104 and Imidacloprid D-36 104 and Indoxacarb D-37104 and Lambda-cyhalothrin D-38 104 and Lufenuron D-39 104 andMetaflumizone D-40 104 and Methomyl D-41 104 and Methoprene D-42 104 andMethoxyfenozide D-43 104 and Nitenpyram D-44 104 and Nithiazine D-45 104and Novaluron D-46 104 and Oxamyl D-47 104 and Pymetrozine D-48 104 andPyrethrin D-49 104 and Pyridaben D-50 104 and Pyridalyl D-51 104 andPyriproxyfen D-52 104 and Ryanodine D-53 104 and Spinetoram D-54 104 andSpinosad D-55 104 and Spirodiclofen D-56 104 and Spiromesifen D-57 104and Tebufenozide D-58 104 and Thiacloprid D-59 104 and Thiamethoxam D-60104 and Thiodicarb D-61 104 and Thiosultap-sodium D-62 104 andTralomethrin D-63 104 and Triazamate D-64 104 and Triflumuron D-65 104and Bacillus thuringiensis D-66 104 and Bacillus thuringiensisdelta-endotoxin D-67 104 and NPV (e.g., Gemstar) E-1 8 and Abamectin E-28 and Acetamiprid E-3 8 and Amitraz E-4 8 and Avermectin E-5 8 andAzadirachtin E-6 8 and Beta-cyfluthrin E-7 8 and Bifenthrin E-8 8 andBuprofezin E-9 8 and Cartap E-10 8 and Chlorantraniliprole E-11 8 andChlorfenapyr E-12 8 and Chlorpyrifos E-13 8 and Clothianidin E-14 8 andCyfluthrin E-15 8 and Cyhalothrin E-16 8 and Cypermethrin E-17 8 andCyromazine E-18 8 and Deltamethrin E-19 8 and Dieldrin E-20 8 andDinotefuran E-21 8 and Diofenolan E-22 8 and Emamectin E-23 8 andEndosulfan E-24 8 and Esfenvalerate E-25 8 and Ethiprole E-26 8 andFenothiocarb E-27 8 and Fenoxycarb E-28 8 and Fenvalerate E-29 8 andFipronil E-30 8 and Flonicamid E-31 8 and Flubendiamide E-32 8 andFlufenoxuron E-33 8 and Hexaflumuron E-34 8 and Hydramethylnon E-35 8and Imidacloprid E-36 8 and Indoxacarb E-37 8 and Lambda-cyhalothrinE-38 8 and Lufenuron E-39 8 and Metaflumizone E-40 8 and Methomyl E-41 8and Methoprene E-42 8 and Methoxyfenozide E-43 8 and Nitenpyram E-44 8and Nithiazine E-45 8 and Novaluron E-46 8 and Oxamyl E-47 8 andPymetrozine E-48 8 and Pyrethrin E-49 8 and Pyridaben E-50 8 andPyridalyl E-51 8 and Pyriproxyfen E-52 8 and Ryanodine E-53 8 andSpinetoram E-54 8 and Spinosad E-55 8 and Spirodiclofen E-56 8 andSpiromesifen E-57 8 and Tebufenozide E-58 8 and Thiacloprid E-59 8 andThiamethoxam E-60 8 and Thiodicarb E-61 8 and Thiosultap-sodium E-62 8and Tralomethrin E-63 8 and Triazamate E-64 8 and Triflumuron E-65 8 andBacillus thuringiensis E-66 8 and Bacillus thuringiensis delta-endotoxinE-67 8 and NPV (e.g., Gemstar) F-1 10 and Abamectin F-2 10 andAcetamiprid F-3 10 and Amitraz F-4 10 and Avermectin F-5 10 andAzadirachtin F-6 10 and Beta-cyfluthrin F-7 10 and Bifenthrin F-8 10 andBuprofezin F-9 10 and Cartap F-10 10 and Chlorantraniliprole F-11 10 andChlorfenapyr F-12 10 and Chlorpyrifos F-13 10 and Clothianidin F-14 10and Cyfluthrin F-15 10 and Cyhalothrin F-16 10 and Cypermethrin F-17 10and Cyromazine F-18 10 and Deltamethrin F-19 10 and Dieldrin F-20 10 andDinotefuran F-21 10 and Diofenolan F-22 10 and Emamectin F-23 10 andEndosulfan F-24 10 and Esfenvalerate F-25 10 and Ethiprole F-26 10 andFenothiocarb F-27 10 and Fenoxycarb F-28 10 and Fenvalerate F-29 10 andFipronil F-30 10 and Flonicamid F-31 10 and Flubendiamide F-32 10 andFlufenoxuron F-33 10 and Hexaflumuron F-34 10 and Hydramethylnon F-35 10and Imidacloprid F-36 10 and Indoxacarb F-37 10 and Lambda-cyhalothrinF-38 10 and Lufenuron F-39 10 and Metaflumizone F-40 10 and MethomylF-41 10 and Methoprene F-42 10 and Methoxyfenozide F-43 10 andNitenpyram F-44 10 and Nithiazine F-45 10 and Novaluron F-46 10 andOxamyl F-47 10 and Pymetrozine F-48 10 and Pyrethrin F-49 10 andPyridaben F-50 10 and Pyridalyl F-51 10 and Pyriproxyfen F-52 10 andRyanodine F-53 10 and Spinetoram F-54 10 and Spinosad F-55 10 andSpirodiclofen F-56 10 and Spiromesifen F-57 10 and Tebufenozide F-58 10and Thiacloprid F-59 10 and Thiamethoxam F-60 10 and Thiodicarb F-61 10and Thiosultap-sodium F-62 10 and Tralomethrin F-63 10 and TriazamateF-64 10 and Triflumuron F-65 10 and Bacillus thuringiensis F-66 10 andBacillus thuringiensis delta-endotoxin F-67 10 and NPV (e.g., Gemstar)G-1 41 and Abamectin G-2 41 and Acetamiprid G-3 41 and Amitraz G-4 41and Avermectin G-5 41 and Azadirachtin G-6 41 and Beta-cyfluthrin G-7 41and Bifenthrin C-8 41 and Buprofezin G-9 41 and Cartap G-10 41 andChlorantraniliprole G-11 41 and Chlorfenapyr G-12 41 and ChlorpyrifosG-13 41 and Clothianidin G-14 41 and Cyfluthrin G-15 41 and CyhalothrinG-16 41 and Cypermethrin G-17 41 and Cyromazine G-18 41 and DeltamethrinG-19 41 and Dieldrin G-20 41 and Dinotefuran G-21 41 and Diofenolan G-2241 and Emamectin G-23 41 and Endosulfan C-24 41 and Esfenvalerate G-2541 and Ethiprole G-26 41 and Fenothiocarb C-27 41 and Fenoxycarb G-28 41and Fenvalerate G-29 41 and Fipronil G-30 41 and Flonicamid G-31 41 andFlubendiamide G-32 41 and Flufenoxuron G-33 41 and Hexaflumuron G-34 41and Hydramethylnon G-35 41 and Imidacloprid G-36 41 and Indoxacarb G-3741 and Lambda-cyhalothrin G-38 41 and Lufenuron G-39 41 andMetaflumizone G-40 41 and Methomyl G-41 41 and Methoprene G-42 41 andMethoxyfenozide G-43 41 and Nitenpyram G-44 41 and Nithiazine G-45 41and Novaluron G-46 41 and Oxamyl G-47 41 and Pymetrozine G-48 41 andPyrethrin G-49 41 and Pyridaben G-50 41 and Pyridalyl G-51 41 andPyriproxyfen G-52 41 and Ryanodine G-53 41 and Spinetoram G-54 41 andSpinosad G-55 41 and Spirodiclofen G-56 41 and Spiromesifen G-57 41 andTebufenozide G-58 41 and Thiacloprid G-59 41 and Thiamethoxam G-60 41and Thiodicarb G-61 41 and Thiosultap-sodium G-62 41 and TralomethrinG-63 41 and Triazamate G-64 41 and Triflumuron G-65 41 and Bacillusthuringiensis G-66 41 and Bacillus thuringiensis delta-endotoxin G-67 41and NPV (e.g., Gemstar) H-1 51 and Abamectin H-2 51 and Acetamiprid H-351 and Amitraz H-4 51 and Avermectin H-5 51 and Azadirachtin H-6 51 andBeta-cyfluthrin H-7 51 and Bifenthrin H-8 51 and Buprofezin H-9 51 andCartap H-10 51 and Chlorantraniliprole H-11 51 and Chlorfenapyr H-12 51and Chlorpyrifos H-13 51 and Clothianidin H-14 51 and Cyfluthrin H-15 51and Cyhalothrin H-16 51 and Cypermethrin H-17 51 and Cyromazine H-18 51and Deltamethrin H-19 51 and Dieldrin H-20 51 and Dinotefuran H-21 51and Diofenolan H-22 51 and Emamectin H-23 51 and Endosulfan H-24 51 andEsfenvalerate D-25 51 and Ethiprole H-26 51 and Fenothiocarb D-27 51 andFenoxycarb H-28 51 and Fenvalerate H-29 51 and Fipronil H-30 51 andFlonicamid H-31 51 and Flubendiamide H-32 51 and Flufenoxuron H-33 51and Hexaflumuron H-34 51 and Hydramethylnon H-35 51 and ImidaclopridH-36 51 and Indoxacarb H-37 51 and Lambda-cyhalothrin H-38 51 andLufenuron H-39 51 and Metaflumizone H-40 51 and Methomyl H-41 51 andMethoprene H-42 51 and Methoxyfenozide H-43 51 and Nitenpyram H-44 51and Nithiazine H-45 51 and Novaluron H-46 51 and Oxamyl H-47 51 andPymetrozine H-48 51 and Pyrethrin H-49 51 and Pyridaben H-50 51 andPyridalyl H-51 51 and Pyriproxyfen H-52 51 and Ryanodine H-53 51 andSpinetoram H-54 51 and Spinosad H-55 51 and Spirodiclofen H-56 51 andSpiromesifen H-57 51 and Tebufenozide H-58 51 and Thiacloprid H-59 51and Thiamethoxam H-60 51 and Thiodicarb H-61 51 and Thiosultap-sodiumH-62 51 and Tralomethrin H-63 51 and Triazamate H-64 51 and TriflumuronH-65 51 and Bacillus thuringiensis H-66 51 and Bacillus thuringiensisdelta-endotoxin H-67 51 and NPV (e.g., Gemstar)

The specific mixtures listed in Table B typically combine a compound ofFormula 1 with the other invertebrate pest agent in the ratios specifiedin Table A.

Invertebrate pests are controlled in agronomic and nonagronomicapplications by applying one or more compounds of this invention,typically in the form of a composition, in a biologically effectiveamount, to the environment of the pests, including the agronomic and/ornonagronomic locus of infestation, to the area to be protected, ordirectly on the pests to be controlled.

Thus the present invention comprises a method for controlling aninvertebrate pest in agronomic and/or nonagronomic applications,comprising contacting the invertebrate pest or its environment with abiologically effective amount of one or more of the compounds of theinvention, or with a composition comprising at least one such compoundor a composition comprising at least one such compound and abiologically effective amount of at least one additional biologicallyactive compound or agent. Examples of suitable compositions comprising acompound of the invention and a biologically effective amount of atleast one additional biologically active compound or agent includegranular compositions wherein the additional active compound is presenton the same granule as the compound of the invention or on granulesseparate from those of the compound of the invention.

To achieve contact with a compound or composition of the invention toprotect a field crop from invertebrate pests, the compound orcomposition is typically applied to the seed of the crop beforeplanting, to the foliage (e.g., leaves, stems, flowers, fruits) of cropplants, or to the soil or other growth medium before or after the cropis planted.

One embodiment of a method of contact is by spraying. Alternatively, agranular composition comprising a compound of the invention can beapplied to the plant foliage or the soil. Compounds of this inventioncan also be effectively delivered through plant uptake by contacting theplant with a composition comprising a compound of this invention appliedas a soil drench of a liquid formulation, a granular formulation to thesoil, a nursery box treatment or a dip of transplants. Of note is acomposition of the present invention in the form of a soil drench liquidformulation. Also of note is a method for controlling an invertebratepest comprising contacting the invertebrate pest or its environment witha biologically effective amount of a compound of the present inventionor with a composition comprising a biologically effective amount of acompound of the present invention. Of further note is this methodwherein the environment is soil and the composition is applied to thesoil as a soil drench formulation. Of further note is that compounds ofthis invention are also effective by localized application to the locusof infestation. Other methods of contact include application of acompound or a composition of the invention by direct and residualsprays, aerial sprays, gels, seed coatings, microencapsulations,systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols,dusts and many others. One embodiment of a method of contact is adimensionally stable fertilizer granule, stick or tablet comprising acompound or composition of the invention. The compounds of thisinvention can also be impregnated into materials for fabricatinginvertebrate control devices (e.g., insect netting).

Compounds of this invention are also useful in seed treatments forprotecting seeds from invertebrate pests. In the context of the presentdisclosure and claims, treating a seed means contacting the seed with abiologically effective amount of a compound of this invention, which istypically formulated as a composition of the invention. This seedtreatment protects the seed from invertebrate soil pests and generallycan also protect roots and other plant parts in contact with the soil ofthe seedling developing from the germinating seed. The seed treatmentmay also provide protection of foliage by translocation of the compoundof this invention or a second active ingredient within the developingplant. Seed treatments can be applied to all types of seeds, includingthose from which plants genetically transformed to express specializedtraits will germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensistoxin or those expressing herbicide resistance such as glyphosateacetyltransferase, which provides resistance to glyphosate.

One method of seed treatment is by spraying or dusting the seed with acompound of the invention (i.e. as a formulated composition) beforesowing the seeds. Compositions formulated for seed treatment generallycomprise a film former or adhesive agent. Therefore typically a seedcoating composition of the present invention comprises a biologicallyeffective amount of a compound of Formula 1, an N-oxide or salt thereof,and a film former or adhesive agent. Seed can be coated by spraying aflowable suspension concentrate directly into a tumbling bed of seedsand then drying the seeds. Alternatively, other formulation types suchas wetted powders, solutions, suspoemulsions, emulsifiable concentratesand emulsions in water can be sprayed on the seed. This process isparticularly useful for applying film coatings on seeds. Various coatingmachines and processes are available to one skilled in the art. Suitableprocesses include those listed in P. Kosters et al., Seed Treatment:Progress and Prospects, 1994 BCPC Mongraph No. 57, and references listedtherein.

The treated seed typically comprises a compound of the present inventionin an amount from about 0.1 g to 1 kg per 100 kg of seed (i.e. fromabout 0.0001 to 1% by weight of the seed before treatment). A flowablesuspension formulated for seed treatment typically comprises from about0.5 to about 70% of the active ingredient, from about 0.5 to about 30%of a film-forming adhesive, from about 0.5 to about 20% of a dispersingagent, from 0 to about 5% of a thickener, from 0 to about 5% of apigment and/or dye, from 0 to about 2% of an antifoaming agent, from 0to about 1% of a preservative, and from 0 to about 75% of a volatileliquid diluent.

The compounds of this invention can be incorporated into a baitcomposition that is consumed by an invertebrate pest or used within adevice such as a trap, bait station, and the like. Such a baitcomposition can be in the form of granules which comprise (a) activeingredients, namely a biologically effective amount of a compound ofFormula 1, an N-oxide, or salt thereof; (b) one or more food materials;optionally (c) an attractant, and optionally (d) one or more humectants.Of note are granules or bait compositions which comprise between about0.001-5% active ingredients, about 40-99% food material and/orattractant; and optionally about 0.05-10% humectants, which areeffective in controlling soil invertebrate pests at very low applicationrates, particularly at doses of active ingredient that are lethal byingestion rather than by direct contact. Some food materials canfunction both as a food source and an attractant. Food materials includecarbohydrates, proteins and lipids. Examples of food materials arevegetable flour, sugar, starches, animal fat, vegetable oil, yeastextracts and milk solids. Examples of attractants are odorants andflavorants, such as fruit or plant extracts, perfume, or other animal orplant component, pheromones or other agents known to attract a targetinvertebrate pest. Examples of humectants, i.e. moisture retainingagents, are glycols and other polyols, glycerine and sorbitol. Of noteis a bait composition (and a method utilizing such a bait composition)used to control at least one invertebrate pest selected from the groupconsisting of ants, termites and cockroaches. A device for controllingan invertebrate pest can comprise the present bait composition and ahousing adapted to receive the bait composition, wherein the housing hasat least one opening sized to permit the invertebrate pest to passthrough the opening so the invertebrate pest can gain access to the baitcomposition from a location outside the housing, and wherein the housingis further adapted to be placed in or near a locus of potential or knownactivity for the invertebrate pest.

The compounds of this invention can be applied without other adjuvants,but most often application will be of a formulation comprising one ormore active ingredients with suitable carriers, diluents, andsurfactants and possibly in combination with a food depending on thecontemplated end use. One method of application involves spraying awater dispersion or refined oil solution of a compound of the presentinvention. Combinations with spray oils, spray oil concentrations,spreader stickers, adjuvants, other solvents, and synergists such aspiperonyl butoxide often enhance compound efficacy. For nonagronomicuses such sprays can be applied from spray containers such as a can, abottle or other container, either by means of a pump or by releasing itfrom a pressurized container, e.g., a pressurized aerosol spray can.Such spray compositions can take various forms, for example, sprays,mists, foams, fumes or fog. Such spray compositions thus can furthercomprise propellants, foaming agents, etc. as the case may be. Of noteis a spray composition comprising a biologically effective amount of acompound or a composition of the present invention and a carrier. Oneembodiment of such a spray composition comprises a biologicallyeffective amount of a compound or a composition of the present inventionand a propellant. Representative propellants include, but are notlimited to, methane, ethane, propane, butane, isobutane, butene,pentane, isopentane, neopentane, pentene, hydrofluorocarbons,chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Ofnote is a spray composition (and a method utilizing such a spraycomposition dispensed from a spray container) used to control at leastone invertebrate pest selected from the group consisting of mosquitoes,black flies, stable flies, deer flies, horse flies, wasps, yellowjackets, hornets, ticks, spiders, ants, gnats, and the like, includingindividually or in combinations.

Nonagronomic applications include protecting an animal, particularly avertebrate, more particularly a homeothermic vertebrate (e.g., mammal orbird) and most particularly a mammal, from an invertebrate parasiticpest by administering a parasiticidally effective (i.e. biologicallyeffective) amount of a compound of the invention, typically in the formof a composition formulated for veterinary use, to the animal to beprotected. Therefore of note is a method for protecting an animalcomprising administering to the animal a parasiticidally effectiveamount of a compound of the invention. As referred to in the presentdisclosure and claims, the terms “parasiticidal” and “parasiticidally”refers to observable effects on an invertebrate parasite pest to provideprotection of an animal from the pest. Parasiticidal effects typicallyrelate to diminishing the occurrence or activity of the targetinvertebrate parasitic pest. Such effects on the pest include necrosis,death, retarded growth, diminished mobility or lessened ability toremain on or in the host animal, reduced feeding and inhibition ofreproduction. These effects on invertebrate parasite pests providecontrol (including prevention, reduction or elimination) of parasiticinfestation or infection of the animal. Examples of invertebrateparasitic pests controlled by administering a parasiticidally effectiveamount of a compound of the invention to an animal to be protectedinclude ectoparasites (arthropods, acarines, etc) and endoparasites(helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans,etc.). In particular, the compounds of this invention are effectiveagainst ectoparasites including: flies such as Haematobia (Lyperosia)irritans (horn fly), Stomoxys calcitrans (stable fly), Simulium spp.(blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly),Musca autumnalis (face fly), Musca domestica (house fly), Morelliasimplex (sweat fly), Tabanus spp. (horese fly), Hypoderma bovis,Hypoderma lineatum, Lucilia sericata, Lucilia Cuprina (green blowfly),Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis (nasalbotfly), Culicoides spp. (midges), Hippobosca equine, Gastrophilusinstestinalis, Gastrophilus haemorrhoidalis and Gastrophilus naslis;lices such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinusasini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosusand Trichodectes canis; keds such as Melophagus ovinus; mites such asPsoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi,Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectescyanotis (ear mites); ticks such as Ixodes spp., Boophilus spp.,Rhipicephalus spp., Amblyomma spp., Dermacentor spp., Hyalomma spp. andHaemaphysalis spp.; fleas such as Ctenocephalides felis (cat flea) andCtenocephalides canis (dog flea).

Nonagronomic applications in the veterinary sector are by conventionalmeans such as by enteral administration in the form of, for example,tablets, capsules, drinks, drenching preparations, granulates, pastes,boli, feed-through procedures, suppositories; or by parenteraladministration, such as by injection (including intramuscular,subcutaneous, intravenous, intraperitoneal), implants; by nasaladministration; by topical administration, for example, in the form ofimmersion or dipping, spraying, washing, coating with powder, orapplication to a small area of the animal, and through articles such asneck collars, ear tags, tail bands, limb bands or halters which comprisecompounds or compositions of the present invention.

Typically a parasiticidal composition according to the present inventioncomprises a mixture of a compound of Formula 1, an N-oxide or a saltthereof, with one or more pharmaceutically or veterinarily acceptablecarriers comprising excipients and auxiliaries selected with regard tothe intended route of administration (e.g., oral, topical or parenteraladministration such as injection) and in accordance with standardpractice. In addition, a suitable carrier is selected on the basis ofcompatibility with the one or more active ingredients in thecomposition, including such considerations as stability relative to pHand moisture content. Therefore of note is a composition for protectingan animal from an invertebrate parasitic pest comprising a parasiticallyeffective amount of a compound of the invention and at least onecarrier.

For parenteral administration including intravenous, intramuscular andsubcutaneous injection, a compound of the present invention can beformulated in suspension, solution or emulsion in oily or aqueousvehicles, and may contain adjuncts such as suspending, stabilizingand/or dispersing agents. Pharmaceutical compositions for injectioninclude aqueous solutions of water-soluble forms of active ingredients(e.g., a salt of an active compound), preferably in physiologicallycompatible buffers containing other excipients or auxiliaries as areknown in the art of pharmaceutical formulation.

For oral administration including solutions (the most readily availableform for absorption), emulsions, suspensions, pastes, gels, capsules,tablets, boluses powders, granules, rumen-retention and feed/water/lickblocks, a compound of the present invention can be formulated withbinders/fillers known in the art to be suitable for oral administrationcompositions, such as sugars (e.g., lactose, sucrose, mannitol,sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potatostarch), cellulose and derivatives (e.g., methylcellulose,carboxymethylcellulose, ethylhydroxycellulose), protein derivatives(e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol,polyvinylpyrrolidone). If desired, lubricants (e.g., magnesiumstearate), disintegrating agents (e.g., cross-linkedpolyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can beadded. Pastes and gels often also contain adhesives (e.g., acacia,alginic acid, bentonite, cellulose, xanthangum, colloidal magnesiumaluminum silicate) to aid in keeping the composition in contact with theoral cavity and not being easily ejected.

If the parasiticidal compositions are in the form of feed concentrates,the carrier is typically selected from high-performance feed, feedcereals or protein concentrates. Such feed concentrate-containingcompositions can, in addition to the parasiticidal active ingredients,comprise additives promoting animal health or growth, improving qualityof meat from animals for slaughter or otherwise useful to animalhusbandry. These additives can include, for example, vitamins,antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostatsand hormones.

Compounds of the present invention have been discovered to havefavorable pharmacokinetic and pharmacodynamic properties providingsystemic availability from oral administration and ingestion. Thereforeafter ingestion by the animal to be protected, parasiticidally effectiveconcentrations of compounds of the invention in the bloodstream protectthe treated animal from blood-sucking pests such as fleas, ticks andlice. Therefore of note is a composition for protecting an animal froman invertebrate parasite pest in a form for oral administration (i.e.comprising, in addition to a parasiticidally effective amount of acompound of the invention, one or more carriers selected from bindersand fillers suitable for oral administration and feed concentratecarriers).

Formulations for topical administration are typically in the form of apowder, cream, suspension, spray, emulsion, foam, paste, aerosol,ointment, salve or gel. More typically a topical formulation is awater-soluble solution, which can be in the form of a concentrate thatis diluted before use. Parasiticidal compositions suitable for topicaladministration typically comprise a compound of the present inventionand one or more topically suitable carriers. In applications of aparasiticidal composition topically to the exterior of an animal as aline or spot (i.e. “spot-on” treatment), the active ingredient isexpected to migrate over the surface of the active to cover most or allof its external surface area. As a result, the treated animal isparticularly protected from invertebrate pests that feed off theepidermis of the animal such as ticks, fleas and lice. Thereforeformulations for topical localized administration often comprise atleast one organic solvent to facilitate transport of the activeingredient over the skin and/or penetration into the epidermis of theanimal. Solvents commonly used as carriers in such formulations includepropylene glycol, paraffins, aromatics, esters such as isopropylmyristate, glycol ethers, and alcohols such as ethanol and n-propanol.

The rate of application required for effective control (i.e.“biologically effective amount”) will depend on such factors as thespecies of invertebrate to be controlled, the pest's life cycle, lifestage, its size, location, time of year, host crop or animal, feedingbehavior, mating behavior, ambient moisture, temperature, and the like.Under normal circumstances, application rates of about 0.01 to 2 kg ofactive ingredients per hectare are sufficient to control pests inagronomic ecosystems, but as little as 0.0001 kg/hectare may besufficient or as much as 8 kg/hectare may be required. For nonagronomicapplications, effective use rates will range from about 1.0 to 50mg/square meter but as little as 0.1 mg/square meter may be sufficientor as much as 150 mg/square meter may be required. One skilled in theart can easily determine the biologically effective amount necessary forthe desired level of invertebrate pest control.

In general for veterinary use, a compound of Formula 1, an N-oxide or asalt thereof, is administered in a parasiticidally effective amount toan animal to be protected from invertebrate parasite pests. Aparasiticidally effective amount is the amount of active ingredientneeded to achieve an observable effect diminishing the occurrence oractivity of the target invertebrate parasite pest. One skilled in theart will appreciate that the parasitically effective dose can vary forthe various compounds and compositions of the present invention, thedesired parasitical effect and duration, the target invertebrate pestspecies, the animal to be protected, the mode of application and thelike, and the amount needed to achieve a particular result can bedetermined through simple experimentation.

For oral administration to homeothermic animals, the daily dosage of acompound of the present invention typically ranges from about 0.01 mg/kgto about 100 mg/kg, more typically from about 0.5 mg/kg to about 100mg/kg, of animal body weight. For topical (e.g., dermal) administration,dips and sprays typically contain from about 0.5 ppm to about 5000 ppm,more typically from about 1 ppm to about 3000 ppm, of a compound of thepresent invention.

The following abbreviations are used in the Index Tables A-C whichfollow: i is iso, t is tert, c is cyclo, Me is methyl, Et is ethyl, c-Pris cyclopropyl and t-Bu is tert-butyl. Naphthyl means naphthalenyl. (R)or (S) denotes the absolute chirality of the asymmetric carbon center.The abbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared. In Index Table A,(R²)_(m) refers to the combination of (R²), with instances of CR² forB¹, B² and B³.

INDEX TABLE A

Compound W (R²)_(m) R⁴ R⁵ m.p. (° C.)  1 (Ex. 1) O 3-Cl, 5-Cl H CH₂CF₃**  2 (Ex. 2) O 3-Cl, 5-Cl H CH₂-2-pyridinyl **  3 O H H CH₂CF₃ *  4 O HH CH₂-2-pyridinyl *  5 O 3-Cl, 5-Cl H CH₂-phenyl *  6 O 3-Cl, 5-Cl HCH₂-3-pyridinyl *  7 O 3-Cl, 5-Cl H CH₂-4-pyridinyl *  8 (Ex. 3) S 3-Cl,5-Cl H CH₂-2-pyridinyl **  9 O 3-Cl, 5-Cl Me Et * 10 O 3-Cl, 5-Cl H Et *11 O 3-Cl, 5-Cl CO₂Me CH2-2-pyridinyl * 12 O 3-Cl, 5-Cl H Me * 13 O3-Cl, 5-Cl H CH₂CH₂N(CH₃)₂ * 14 O 3-Cl, 5-Cl H CH₂CH₂N(CH₃)₂•HCl * 15 O3-Cl, 5-Cl H (R)-CH(CH₃)-phenyl * 16 O 3-Cl, 5-Cl H CH(CH₃)₂ * 17 O3-Cl, 5-Cl H (S)-CH(CH₃)-phenyl * 18 O 3-Cl, 5-Cl H CH₂CH═CH₂ * 19 O3-Cl, 5-Cl H CH₂C≡CH * 20 O 3-Cl, 5-Cl H CH₂-c-Pr * 21 O 3-Cl, 5-Cl HCH(CH₃)-2-pyridinyl * 22 O 3-Me, 5-Me H CH₂-2-pyridinyl * 23 O 3-Cl,4-Cl H CH₂-2-pyridinyl * 24 O 3-F, 5-F H CH₂-2-pyridinyl * 25 O 3-Cl HCH₂-2-pyridinyl * 26 O 3-Br, 5-Br H CH₂-2-pyridinyl * 27 O 3-Cl, 5-Cl H(R)-CH(CH₃)-2-naphthyl * 28 O 3-Cl, 5-Cl H (R)-CH(CH₃)-(4-NO₂-phenyl) *29 O 3-Cl, 5-Cl H (S)-CH(CO₂CH₃)-phenyl * 30 O 3-Cl, 5-Cl H(R)-CH(CH₃)-(4-Cl-phenyl) * 31 O 3-Cl, 5-Cl H (R)-CH(CH₃)-(4-F-phenyl) *32 O 3-Cl, 5-Cl H (R)-CH(CH₃)CH₂CH₃ * 33 O 3-Cl, 5-Cl H CH(CH₃)CH₂CH₃ *34 O 3-Cl, 5-Cl H (R)-CH(CH₃)-t-Bu * 35 O 3-Cl, 5-Cl H CH₂CH₂OH * 36 O3-Cl, 5-Cl H H * 37 O 3-Cl, 5-Cl —CH₂CH₂N(CH₃)CH₂CH₂— * 38 O 3-Cl, 5-ClH

* 39 O 3-Cl, 5-Cl H

* 40 O 3-Cl, 5-Cl H

* 41 O 3-Cl, 5-Cl H CH₂CH₂OCH₃ * 42 O 3-Cl, 5-Cl H CH₂CO₂Et * 43 O 3-Cl,5-Cl H CH₂CO₂H * 44 O 3-Cl, 5-Cl H CH₂CO₂Na * 45 O 3-Cl, 5-Cl HNHC(═O)Me * 46 O 3-Cl, 5-Cl H NH-phenyl * 47 O 3-Cl, 5-Cl H CH₂CH₂NH₂ *48 O 3-Cl, 5-Cl H (S)-CH(Me)CO₂Me * 49 O 3-Cl, 5-Cl H(S)-CH(i-Pr)CO₂Me * 50 O 3-Cl, 5-Cl H CH₂(CH₂)₅NH₂ * 51 O 3-Cl, 5-Cl HCH₂CONHCH₂CF₃ * 52 O 3-Cl, 5-Cl H CH₂CN * 53 O 3-Cl, 5-Cl HNH-2-pyridinyl * *See Index Table D for ¹H NMR data. **See Examples for¹H NMR data.

INDEX TABLE B

Com- m.p. pound W A¹ A² A³ A⁴ A⁵ A⁶ R⁴ R⁵ (° C.) 101 O N CH CH CH CH CHH CH₂-2-pyridinyl * 102 O CH N CH CH CH CH H CH₂-2-pyridinyl * 103 O CHCH N CH CH CH H CH₂-2-pyridinyl ** (Ex. 4) 104 O CH CH CH N CH CH HCH₂-2-pyridinyl ** (Ex. 5) 105 O CH CH CH CH N CH H CH₂-2-pyridinyl *106 O CH CH CH CH CH N H CH₂-2-pyridinyl * 107 O CH CH CH CH CH N HCH₂CF₃ * 108 S CH CH CH CH CH N H CH₂-2-pyridinyl * 109 S CH CH CH CH CHN H CH₂CF₃ * 110 O CH CCH₃ CH CH CH CH H CH₂-2-pyridinyl * 111 O CH CCH₃CH CH CH CH H CH₂CF₃ * *See Index Table D for ¹H NMR data. **SeeExamples for ¹H NMR data.

INDEX TABLE C

Compound B¹ B² B³ (R²)_(n) R⁴ R⁵ m.p. (° C.) 201 C—Cl N CH H H CH₂CF₃ *202 C—Cl N CH H H CH₂-2-pyridinyl * *See Index Table D for ¹H NMR data.

INDEX TABLE D Compd. No. ¹H NMR Data (CDCl₃ solution unless indicatedotherwise)^(a) 3 δ 8.67 (d, 1H), 8.06 (d, 1H), 7.66-7.45 (m, 7H), 7.39(d, 1H), 7.29 (d, 1H), 6.78 (br s 1H), 4.19 (d, 1H), 4.15 (m, 2H), 3.88(d, 1H). 4 δ 8.82 (d, 1H), 8.50 (d, 1H), 8.35 (d, 1H), 7.71-7.44 (m,11H), 7.35 (d, 1H), 7.20 (dd, 1H), 4.83 (d, 2H), 4.25 (d, 1H), 3.95 (d,1H). 5 δ 8.78 (d, 1H), 8.27 (d, 1H), 7.64-7.30 (m, 12H), 6.40 (br t 1H),4.71 (d, 2H), 4.22 (d, 1H), 3.86 (d, 1H). 6 δ 8.72 (d, 1H), 8.53 (d,1H), 8.49 (dd, 1H), 8.18 (d, 1H), 7.72 (d, 1H), 7.60-7.52 (m, 4H), 7.45(m, 2H), 7.36 (d, 1H), 7.27 (m, 1H), 6.93 (br t, 1H), 4.66 (d, 2H), 4.21(d, 1H), 3.86 (d, 1H). 7 δ 8.72 (d, 1H), 8.50 (d, 2H), 8.19 (d, 1H),7.61-7.54 (m, 4H), 7.47 (m, 2H), 7.37 (d, 1H), 7.23 (d, 2H), 7.02 (br t,1H), 4.66 (d, 2H), 4.22 (d, 1H), 3.86 (d, 1H). 9 δ 8.88 (m, 1H), 7.83(m, 1H), 7.66-7.40 (m, 7H), 4.27 (d, 1H), 3.92 (d, 1H), 3.80-3.66 and3.09 (m, 2H), 3.22 and 2.74 (s, 3H), 1.01 and 1.36 (t, 3H). 10 δ 8.78(d, 1H), 8.25 (d, 1H), 7.64-7.42 (m, 7H), 6.08 (br s, 1H), 4.24 (d, 1H),3.88 (d, 1H), 3.58 (m, 2H), 1.31 (t, 3H). 11 δ 8.92 (d, 1H), 8.63 (d,1H), 8.17 (d, 1H), 7.74-7.53 (m, 7H), 7.45 (t, 1H), 7.35 (d, 1H), 7.23(dd, 1H), 5.33 (s, 2H), 4.29 (d, 1H), 3.92 (d, 1H), 3.43 (s, 3H). 12 δ8.77 (d, 1H), 8.21 (d, 1H), 7.63-7.55 (m, 5H), 7.44 (d, 1H), 7.38 (d,1H), 6.18 (br s, 1H), 4.23 (d, 1H), 3.87 (d, 1H), 3.07 (d, 3H). 13 δ8.78 (d, 1H), 8.27 (d, 1H), 7.39-7.62 (m, H), 6.77 (br s, 1H), 4.22 (d,1H), 3.88 (d, 1H), 3.58 (q, 2H), 2.53 (t, 2H), 2.25 (s, 6H). 15 δ 8.63(dd, 1H), 8.00 (dd, 1H), 7.56 (s, 2H), 7.47-7.16 (m, 9H), 6.78 (dd, 1H),5.34 (m, 1H), 4.14 (dd, 1H), 3.80 (dd, 1H), 1.60 (d, 3H). 16 δ 8.80 (d,1H), 8.25 (d, 1H), 7.66-7.45 (m, 7H), 5.87 (d, 1H), 4.41 (m, 1H), 4.24(d, 1H), 3.88 (d, 1H), 1.33 (d, 6H). 17 δ 8.77 (d, 1H), 8.19 (dd, 1H),7.63-7.30 (m, 12H), 6.30 (d, 1H), 5.44 (m, 1H), 4.22 (d, 1H), 3.86 (d,1H), 1.67 (d, 1H). 18 δ 8.80 (d, 1H), 8.27 (d, 1H), 7.67-7.45 (m, 7H),6.15 (br t, 1H), 5.99 (m, 1H), 5.31 (d, 1H), 5.24 (d, 1H), 4.25 (d, 1H),4.17 (m, 2H), 3.88 (d, 1H). 19 δ 8.77 (d, 1H), 8.24 (d, 1H), 7.64-7.56(m, 4H), 7.50 (d, 1H), 7.46 (dd, 1H), 7.40 (d, 1H), 6.38 (br t, 1H),4.33 (dd, 2H), 4.23 (d, 1H), 3.87 (d, 1H), 2.32 (t, 1H). 20 δ 8.82 (d,1H), 8.29 (d, 1H), 7.67-7.45 (m, 7H), 6.14 (br s, 1H), 4.26 (d, 1H),3.90 (d, 1H), 3.42 (dd, 2H), 1.12 (m, 1H), 0.59 (m, 2H), 0.32 (m, 2H).21 δ 8.82 (d, 1H), 8.50 (d, 1H), 8.34 (d, 1H), 7.72 (dt, 1H), 7.67-7.57(m, 6H), 7.50 (d, 1H), 7.45 (dd, 1H), 7.34 (d, 1H), 7.21 (dd, 1H), 5.45(m, 1H), 4.26 (d, 1H), 3.90 (d, 1H), 1.66 (d, 3H). 22 δ 8.85 (d, 1H),8.51 (d, 1H), 8.36 (d, 1H), 7.72-7.57 (m, 4H), 7.51 (d, 1H), 7.45 (br t,1H), 7.36 (d, 1H), 7.25 (s, 2H), 7.21 (dd, 1H), 7.07 (s, 1H), 4.85 (d,1H), 4.22 (d, 1H), 3.94 (d, 1H), 2.38 (s, 6H). 23 δ 8.81 (d, 1H), 8.51(d, 1H), 8.37 (d, 1H), 7.78-7.46 (m, 9H), 7.36 (d, 1H), 7.22 (dd, 1H),4.85 (d, 2H), 4.26 (d, 1H), 3.90 (d, 1H). 24 δ 8.83 (d, 1H), 8.52 (d,1H), 8.39 (d, 1H), 7.74-7.22 (m, H), 6.91 (dt, 1H), 4.87 (d, 2H), 4.27(d, 1H), 3.90 (d, 1H). 25 δ 8.83 (d, 1H), 8.51 (d, 1H), 8.37 (d, 1H),7.73-7.41 (m, 10H), 7.37 (d, 1H), 7.22 (dd, 1H), 4.86 (d, 2H), 4.26 (d,1H), 3.92 (d, 1H). 26 δ 8.82 (d, 1H), 8.52 (d, 1H), 8.38 (d, 1H), 7.76(s, 2H), 7.74-7.59 (m, H), 7.52 (d, 1H), 7.44 (br t, 1H), 7.37 (d, 1H),7.23 (dd, 1H), 4.87 (d, 2H), 4.26 (d, 1H), 3.90 (d, 1H). 27 δ 8.76 (d,1H), 8.19 (dd, 1H), 7.87-7.36 (m, 14H), 6.46 (d, 1H), 5.59 (m, 1H), 4.20(d, 1H), 3.84 (d, 1H), 1.73 (d, 3H). 28 δ 8.77 (d, 1H), 8.23 (d, 2H),8.14 (dd, 1H), 7.66-7.44 (m, 9H), 6.45 (d, 1H), 5.47 (m, 1H), 4.24 (d,1H), 3.88 (d, 1H), 1.66 (d, 3H). 29 δ 8.80 (d, 1H), 8.28 (d, 1H),7.66-7.37 (m, H), 6.99 (d, 1H), 5.87 (d, 1H), 4.24 (d, 1H), 3.88 (d,1H), 3.80 (s, 3H). 30 δ 8.76 (d, 1H), 8.14 (dd, 1H), 7.63-7.35 (m, 11H),6.35 (d, 1H), 5.38 (m, 1H), 4.21 (d, 1H), 3.85 (d, 1H), 1.62 (d, 3H). 31δ 8.76 (d, 1H), 8.16 (dd, 1H), 7.64-7.38 (m, 9H), 7.07 (d, 1H), 7.05 (d,1H), 6.30 (d, 1H), 5.41 (m, 1H), 4.22 (d, 1H), 3.86 (d, 1H), 1.64 (d,3H). 32 δ 8.81 (d, 1H), 8.26 (d, 1H), 7.67-7.45 (m, 7H), 5.78 (d, 1H),4.26 (d, 1H), 4.25 (m, 1H), 3.88 (d, 1H), 1.63 (m, 2H), 1.30 (d, 3H),1.04 (t, 3H). 33 δ 8.81 (d, 1H), 8.26 (d, 1H), 7.67-7.45 (m, 7H), 5.78(d, 1H), 4.26 (d, 1H), 4.25 (m, 1H), 3.88 (d, 1H), 1.63 (m, 2H), 1.30(d, 3H), 1.04 (t, 3H). 34 δ 8.80 (d, 1H), 8.26 (d, 1H), 7.68-7.46 (m,7H), 5.80 (d, 1H), 4.26 (d, 1H), 4.23 (m, 1H), 3.88 (d, 1H), 1.24 (d,3H), 1.01 (s, 9H). 35 δ 8.65 (d, 1H), 8.08 (d, 1H), 7.55 (s, 2H),7.52-7.44 (m, 7H), 7.27 (d, 1H), 7.19 (d, 1H), 6.93 (br t, 1H), 4.16 (d,1H), 3.81 (d, 1H), 3.73 (s, br, 2H), 3.53 (m, 2H), 3.27 (br s, 1H). 36 δ8.75 (d, 1H), 8.30 (d, 1H), 7.63-7.35 (m, 7H), 6.69 (br s, 1H), 6.32 (brs, 1H), 4.22 (d, 1H), 3.86 (d, 1H). 38 δ 8.79 (m, 1H), 8.34 (d, 1H),7.64-7.12 (m, 11H), 6.29 (dd, 1H), 5.50 (m, 1H), 4.22 (d, 1H), 3.87 (d,1H), 2.82 (m, 2H), 2.24 (m, 1H), 2.05 (m, 1H), 1.91 (m, 2H). 39 δ 8.80(d, 1H), 8.34 (d, 1H), 7.65-7.25 (m, H), 6.28 (d, 1H), 5.79 (q, 1H),4.24 (d, 1H), 3.87 (d, 1H), 3.92-3.07 (m, 2H), 2.77 (m, 1H), 1.99 (m,1H). 40 δ 8.81 (d, 1H), 8.37 (d, 1H), 7.67-7.26 (m, H), 6.26 (d, 1H),5.80 (q, 1H), 4.24 (d, 1H), 3.88 (d, 1H), 3.09-2.93 (m, 2H), 2.79 (m,1H), 1.99 (m, 1H). 41 δ 8.82 (d, 1H), 8.30 (d, 1H), 7.67-7.46 (m, 7H),6.40 (br t, 1H), 4.25 (d, 1H), 3.89 (d, 1H), 3.75 (q, 2H), 3.63 (dd,2H), 3.39 (s, 3H). 42 δ 8.84 (d, 1H), 8.37 (d, 1H), 7.67-7.46 (m, 7H),6.53 (br t, 1H), 4.33 (d, 2H), 4.29 (q, 2H), 4.26 (d, 1H), 3.90 (d, 1H),1.34 (t, 3H). 43 DMSO-d₆: δ 9.02 (t, 1H), 8.81 (d, 1H), 8.37 (d, 1H),7.92 (d, 1H), 7.83 (t, 1H), 7.74-7.65 (m, 5H), 4.58 (d, 1H), 4.54 (d,1H), 4.02 (d, 2H). 44 DMSO-d₆: δ 8.86 (d, 1H), 8.50 (d, 1H), 7.96-7.67(m, 8H), 4.61 (apparent s, 2H), 3.64 (d, 2H). 45 DMSO-d₆ δ 10.44 (s,1H), 10.10 (s, 1H), 8.86 (d, 1H), 8.46 (d, 1H), 7.98 (d, 1H), 7.90 (t,1H), 7.76 (m, 5H), 4.63 (d, 1H), 4.59 (d, 1H), 2.04 (s, 3H). 46 δ 10.45(s, 1H), 8.80 (d, 1H), 8.24 (d, 1H), 7.95 (d, 1H), 7.85-7.63 (m, 7H),7.22 (t, 2H), 6.90 (d, 2H), 6.78 (t, 1H), 4.57 (apparent s, 2H). 47 δ8.83 (d, 1H), 8.33 (d, 1H), 7.69-7.46 (m, 9H), 6.54 (br s, 1H), 4.27 (d,1H), 3.90 (d, 1H), 3.61 (q, 2H), 3.02 (t, 3H). 48 δ 8.83 (d, 1H), 8.35(d, 1H), 7.68-7.46 (m, 7H), 6.54 (d, 1H), 4.91 (m, 1H), 4.26 (d, 1H),3.90 (d, 1H), 3.83 (s, 3H), 1.60 (d, 3H). 49 δ 8.84 (d, 1H), 8.34 (d,1H), 7.70-7.46 (m, 7H), 6.46 (d, 1H), 4.91 (dd, 1H), 4.26 (d, 1H), 3.90(d, 1H), 3.83 (s, 3H), 2.36 (m, 1H), 1.10 (d, 3H), 0.99 (d, 3H). 50DMSO-d₆ δ 8.79 (d, 1H), 8.71 (t, 1H), 8.19 (d, 1H), 8.08 (br s, 2H),7.90 (d, 1H), 7.84 (dd, 1H), 7.73-7.66 (m, 4H), 7.62 (d, 1H), 4.54(apparent s, 2H), 3.35 (m, 2H), 2.76 (m, 2H), 1.60 (m, 4H), 1.39 (m,4H). 51 δ 8.82 (d, 1H), 8.26 (d, 1H), 7.67-7.46 (m, 7H), 7.09 (m, 2H),4.28 (d, 2H), 4.25 (d, 1H), 3.96 (m, 2H), 3.88 (d, 1H). 52 δ 8.79 (d,1H), 8.23 (d, 1H), 7.68-7.46 (m, 7H), 6.53 (br t, 1H), 4.46 (d, 2H),4.26 (d, 1H), 3.89 (d, 1H). 53 δ 8.83 (d, 1H), 8.42 (d, 1H), 8.18 (d,1H), 7.73 (d, 1H), 7.70-7.55 (m, 7H), 7.50 (d, 1H), 7.46 (dd, 1H), 6.84(dd, 1H), 6.80 (d, 1H), 4.26 (d, 1H), 3.90 (d, 1H). 101 δ 9.24 (d, 1H),8.75 (s, 1H), 8.52 (d, 1H), 8.45 (d, 1H), 7.82-7.70 (m, 3H), 7.64 (br s,1H), 7.58 (s, 2H), 7.44 (t, 1H), 7.37 (d, 1H), 7.24 (dd, 1H), 4.87 (d,2H), 102 δ 9.63 (d, 1H), 9.04 (br t, 1H), 8.93 (d, 1H), 8.60 (d, 1H),8.52 (s, 1H), 7.86 (dd, 1H), 7.74 (dd, 1H), 7.69 (dd, 1H), 7.57 (s, 2H),7.46 (dd, 1H), 7.40 (d, 1H), 7.23 (dd, 1H), 4.85 (d, 2H), 4.31 (d, 1H),3.94 (d, 1H). 105 δ 10.17 (s, 1H), 8.64 (d, 1H), 8.53 (d, 1H), 8.22 (d,1H), 7.90 (d, 1H), 7.73 (dt, 1H), 7.68 (br t, 1H), 7.59 (d, 1H), 7.56(s, 2H), 7.46 (t, 1H), 7.37 (d, 1H), 7.24 (dd, 1H), 4.85 (d, 2H), 4.27(d, 1H), 3.92 (d, 1H). 106 δ 8.95 (dd, 1H), 8.88 (dd, 1H), 8.55 (d, 1H),8.26 (d, 1H), 7.83 (d, 1H), 7.72 (dt, 1H), 7.60-7.50 (m, 4H), 7.43 (t,1H), 7.36 (d, 1H), 7.24 (dd, 1H), 4.85 (d, 2H), 4.72 (d, 1H), 4.42 (d,1H). 107 δ 8.89 (dd, 1H), 8.61 (d, 1H), 7.99 (d, 1H), 7.59 (d, 1H), 7.55(s, 2H), 7.45 (m, 2H), 6.89 (br t, 1H), 4.68 (d, 1H), 4.32 (d, 1H), 4.18(m, 2H). 108 δ 9.41 (br s, 1H), 8.91 (dd, 1H), 8.70 (dd, 1H), 8.46 (d,1H), 8.21 (d, 1H), 7.75 (dt, 1H), 7.64 (d, 1H), 7.57 (s, 2H), 7.47 (dd,1H), 7.43 (t, 1H), 7.38 (d, 1H), 7.24 (dd, 1H), 5.14 (d, 2H), 4.68 (d,1H), 4.39 (d, 1H). 109 δ 8.88 (d, 1H), 8.47 (dd, 1H), 8.12 (br s, 1H),7.97 (d, 1H), 7.53 (s, 2H), 7.47 (m, 3H), 4.74 (m, 2H), 4.59 (d, 1H),4.25 (d, 1H). 110 δ 8.75 (d, 1H), 8.42 (d, 1H), 7.86 (d, 1H), 7.68 (dt,1H), 7.57 (s, 2H), 7.55-7.35 (m, 5H), 7.31 (s, 1H), 7.18 (dd, 1H), 4.82(d, 2H), 4.25 (d, 1H), 3.90 (d, 1H), 2.44 (s, 3H). 111 δ 8.59 (d, 1H),7.58 (s, 2H), 7.54 (d, 1H), 7.47 (t, 1H), 7.36-7.44 (m, 2H), 7.10 (s,1H), 6.80 (br t, 1H), 4.20 (d, 1H), 4.08 (m, 2H), 3.86 (d, 1H), 2.23 (s,3H). 201 δ 8.71 (d, 1H), 8.48 (m, 1H), 8.13 (d, 1H), 7.55-7.64 (m, 3H),7.49 (d, 1H), 7.44 (d, 1H), 7.35 (dd, 1H), 6.74 (t, 1H), 4.24 (d, 1H),4.17 (m, 2H), 3.83 (d, 1H). 202 δ 8.79 (d, 1H), 8.50 (m, 2H), 8.35 (d,1H), 7.50-7.72 (m, 7H), 7.47 (d, 1H), 7.36 (d, 1H), 7.22 (dd, 1H), 4.83(d, 2H), 4.28 (d, 1H), 3.89 (d, 1H). ^(a1)H NMR data are in ppmdownfield from tetramethylsilane. Couplings are designated by(s)—singlet, (d)—doublet, (t)—triplet, (q)—quartet, (m)—multiplet,(dd)—doublet of doublets, (dt)—doublet of triplets, (br s)—broadsinglet, (br t)—broad triplet.

BIOLOGICAL EXAMPLES OF THE INVENTION

The following Tests demonstrate the control efficacy of compounds ofthis invention on specific pests. “Control efficacy” representsinhibition of invertebrate pest development (including mortality) thatcauses significantly reduced feeding. The pest control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-C for compound descriptions.

Test A

For evaluating control of diamondback moth (Plutella xylostella) thetest unit consisted of a small open container with a 12-14-day-oldradish plant inside. This was pre-infested with about 50 neonate larvaethat were dispensed into the test unit via corn cob grits using abazooka inoculator. The larvae moved onto the test plant after beingdispensed into the test unit.

Test compounds were formulated using a solution containing 10% acetone,90% water and 300 ppm X77™ Spreader Lo-Foam Formula non-ionic surfactantcontaining alkylarylpolyoxyethylene, free fatty acids, glycols andisopropanol (Loveland Industries, Inc. Greeley, Colorado, USA). Theformulated compounds were applied in 1 mL of liquid through a SUJ2atomizer nozzle with ⅛ JJ custom body (Spraying Systems Co. Wheaton,Ill., USA) positioned 1.27 cm (0.5 inches) above the top of each testunit. All experimental compounds in these tests were sprayed at 250and/or 50 ppm, and the test was replicated three times. After sprayingof the formulated test compound, each test unit was allowed to dry for 1h and then a black, screened cap was placed on top. The test units wereheld for 6 days in a growth chamber at 25° C. and 70% relative humidity.Plant feeding damage was then visually assessed based on foliageconsumed and a pest mortality rating was also counted and calculated foreach test unit.

Of the compounds of Formula 1 tested the following provided very good toexcellent levels of control efficacy (20% or less feeding damage or 80%or more mortality): 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16,18, 19, 20, 21, 22, 23, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38,39, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 101, 102, 103, 104, 105,106, 107*, 108*, 109*, 110, 111, 201 and 202.

* means very good to excellent levels of control efficacy observed onlyat 250 ppm.

Test B

For evaluating control of fall armyworm (Spodoptera frugiperda) the testunit consisted of a small open container with a 4-5-day-old corn (maize)plant inside. This was pre-infested (using a core sampler) with 10-151-day-old larvae on a piece of insect diet. Test compounds wereformulated and sprayed at 250 and/or 50 ppm as described for Test A andreplicated three times. After spraying, the test units were maintainedin a growth chamber and then the control efficacy was rated for eachtest unit as described for Test A.

Of the compounds of Formula 1 tested the following provided very good toexcellent levels of control efficacy (20% or less feeding damage or 80%or more mortality): 1, 2, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18,19, 20, 21, 22, 23, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 39, 41,42, 46, 49, 51, 101, 102, 103, 104, 106*, 107*, 110*, 111*, 201 and 202.

*means very good to excellent levels of control efficacy observed onlyat 250 ppm.

Test C

For evaluating control of potato leafhopper (Empoasca fabae Harris)through contact and/or systemic means, the test unit consisted of asmall open container with a 5-6 day old Soleil bean plant (primaryleaves emerged) inside. White sand was added to the top of the soil andone of the primary leaves was excised prior to application. Testcompounds were formulated and sprayed at 250 and/or 50 ppm, and the testwas replicated three times as described for Test A. After spraying, thetest units were allowed to dry for 1 hour before they were post-infestedwith 5 potato leafhoppers (18- to 21-day old adults). A black, screenedcap was placed on the top of the cylinder. The test units were held for6 days in a growth chamber at 19-21° C. and 50-70% relative humidity.The control efficacy of each test unit was then visually assessed by theinsect mortality.

Of the compounds of Formula 1 tested the following provided very good toexcellent levels of control efficacy (80% or more mortality): 1, 2, 8,10, 11, 14*, 15, 16, 18*, 19, 20, 21, 26, 28, 31, 32*, 34, 36, 38, 46*,101, 102* and 106*.

* means very good to excellent levels of control efficacy observed onlyat 250 ppm.

Test D

For evaluating control of the western flower thrips (Frankliniellaoccidentalis) through contact and/or systemic means, the test unitconsisted of a small open container with a 5-7 day old Soleil Bean plantinside. Test compounds were formulated and sprayed at 250 and/or 50 ppm,and the test was replicated three times as described for Test A. Afterspraying, the test units were allowed to dry for 1 hour and then 22-27adult thrips were added to each unit and then a black, screened cap wasplaced on top. The test units were held for 6 days at 25° C. and 45-55%relative humidity. A mortality rating was assessed along with a plantdamage rating for each test unit.

Of the compounds of Formula 1 tested the following provided very good toexcellent levels of control efficacy (20% or less feeding damage or 80%or more mortality): 1, 2, 8, 10, 11, 13*, 14*, 15*, 16, 18, 19, 20*, 21,26, 32, 33*, 34*, 35, 39*, 41, 42, 45*, 46*, 47*, 48*, 49, 51, 101 and104.

* means very good to excellent levels of control efficacy observed onlyat 250 ppm.

Test E

For evaluating control of the cat flea (Ctenocephalides felis Bouche), aCD-1® mouse (about 30 g, male, obtained from Charles River Laboratories,Wilmington, Mass.) was orally dosed with a test compound in an amount of10 mg/kg solubilized in propylene glycol/glycerol formal (60:40). Twohours after oral administration of the test compound, approximately 8 to16 adult fleas were applied to each mouse. The fleas were then evaluatedfor mortality 48 hours after flea application to the mouse.

Of the compounds tested, the following compounds caused 30% or moremortality: 1*, 2, 10*, 41* and 51*.

* means the compound caused 50% or more mortality.

1. A compound of Formula 1, an N-oxide, or a salt thereof,

wherein A¹, A², A³, A⁴, A⁵ and A⁶ are independently selected from thegroup consisting of CR³ and N, provided that at most 3 of A¹, A², A³,A⁴, A⁵ and A⁶ are N; B¹, B² and B³ are independently selected from thegroup consisting of CR² and N; W is O or S; R¹ is C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R⁶; each R² is independently H,halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy,C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆ dialkylamino, C₂-C₄ alkoxycarbonyl, —CN or —NO₂; eachR³ is independently H, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆alkylamino, C₂-C₆ dialkylamino, —CN or —NO₂; R⁴ is H, C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl; R⁵ is H,OR¹⁰, NR¹¹R¹² or Q¹; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R⁷; or R⁴ and R⁵ are taken together with the nitrogen towhich they are attached to form a ring containing 2 to 6 atoms of carbonand optionally one additional atom selected from the group consisting ofN, S and O, said ring optionally substituted with 1 to 4 substituentsindependently selected from the group consisting of C₁-C₂ alkyl,halogen, —CN, —NO₂ and C₁-C₂ alkoxy; each R⁶ is independently halogen,C₁-C₆ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆alkylsulfonyl, —CN or —NO₂; each R⁷ is independently halogen, C₁-C₆alkyl, C₃-C₆ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₇ alkylcarbonyl, C₂-C₇alkoxycarbonyl, C₂-C₇ alkylaminocarbonyl, C₃-C₉ dialkylaminocarbonyl,C₂-C₇ haloalkylcarbonyl, C₂-C₇ haloalkoxycarbonyl, C₂-C₇haloalkylaminocarbonyl, C₃-C₉ halodialkylaminocarbonyl, hydroxy, —NH₂,—CN or —NO₂; or Q²; each R⁸ is independently halogen, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₄alkoxycarbonyl, —CN or —NO₂; each R⁹ is independently halogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆ halocycloalkyl, C₁-C₆alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, —CN, —NO₂,phenyl or pyridinyl; R¹⁰ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or more halogen;R¹¹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl,C₄-C₇ alkylcycloalkyl, C₄-C₇ cycloalkylalkyl, C₂-C₇ alkylcarbonyl orC₂-C₇ alkoxycarbonyl; R¹² is H; Q³; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇cycloalkylalkyl, each optionally substituted with one or moresubstituents independently selected from R⁷; or R¹¹ and R¹² are takentogether with the nitrogen to which they are attached to form a ringcontaining 2 to 6 atoms of carbon and optionally one additional atomselected from the group consisting of N, S and O, said ring optionallysubstituted with 1 to 4 substituents independently selected from thegroup consisting of C₁-C₂ alkyl, halogen, —CN, —NO₂ and C₁-C₂ alkoxy; Q¹is a phenyl ring, a 5- or 6-membered heterocyclic ring, or an 8-, 9- or10-membered fused bicyclic ring system optionally containing one tothree heteroatoms selected from up to 1 O, up to 1 S and up to 3 N, eachring or ring system optionally substituted with one or more substituentsindependently selected from R⁸; each Q² is independently a phenyl ringor a 5- or 6-membered heterocyclic ring, each ring optionallysubstituted with one or more substituents independently selected fromR⁹; Q³ is a phenyl ring or a 5- or 6-membered heterocyclic ring, eachring optionally substituted with one or more substituents independentlyselected from R⁹; and n is 0, 1 or
 2. 2. A compound of claim 1 whereinR¹ is C₁-C₃ alkyl optionally substituted with one or more substituentsindependently selected from R⁶; each R² is independently H, halogen,C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy or —CN; and each R³ is independentlyH, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, —CN or —NO₂.
 3. Acompound of claim 2 wherein B¹, B² and B³ are independently CR²; W is O;R⁴ is H, C₁-C₆ alkyl, C₂-C₇ alkylcarbonyl or C₂-C₇ alkoxycarbonyl; andR⁵ is H, NR¹¹R¹² or Q¹; or C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl,C₃-C₄ cycloalkyl, C₄-C₇ alkylcycloalkyl or C₄-C₇ cycloalkylalkyl, eachoptionally substituted with one or more substituents independentlyselected from R⁷.
 4. A compound of claim 3 wherein R¹ is C₁-C₃ alkyloptionally substituted with halogen; each R² is independently H, CF₃,OCF₃, halogen or —CN; each R³ is independently H, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₃-C₆ cyclopropyl, C₁-C₄ alkoxy or —CN; and each R⁷ isindependently halogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkylcarbonyl, C₂-C₄alkoxycarbonyl, C₂-C₅ alkylaminocarbonyl, C₂-C₅ haloalkylcarbonyl, C₂-C₅haloalkoxycarbonyl, C₂-C₅ haloalkylaminocarbonyl, —NH₂, —CN or —NO₂; orQ².
 5. A compound of claim 4 wherein R⁴ is H; R⁵ is C₁-C₄ alkyloptionally substituted with one of more substituents independentlyselected from R⁷; each R⁷ is independently halogen or Q²; and each Q² isindependently phenyl, pyridinyl or thiazolyl.
 6. A compound of claim 5wherein R¹ is CF₃; A¹, A², A³, A⁴, A⁵ and A⁶ are each CR³; B² is CR²;and each R³ is independently H, C₁-C₄ alkyl or —CN.
 7. A compound ofclaim 6 wherein B² is CH; each R² is independently halogen or C₁-C₃haloalkyl; R³ is H; R⁵ is CH₂CF₃ or CH₂-2-pyridinyl; and n is
 0. 8. Acompound of claim 1 that is selected from the group consisting of:4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarboxamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-1-naphthalenecarbothioamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-ethyl-1-naphthalenecarboxamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-methoxyethyl)-1-naphthalenecarboxamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(2,2,2-trifluoroethyl)-2-oxoethyl]-1-naphthalenecarboxamide,5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-quinolinecarboxamide,5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-8-isoquinolinecarboxamide,and1-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2-pyridinylmethyl)-4-isoquinolinecarboxamide.9. A composition comprising a compound of claim 1 and at least oneadditional component selected from the group consisting of a surfactant,a solid diluent and a liquid diluent, said composition optionallyfurther comprising at least one additional biologically active compoundor agent.
 10. A composition for controlling an invertebrate pestcomprising a biologically effective amount of a compound of claim 1 andat least one additional component selected from the group consisting ofa surfactant, a solid diluent and a liquid diluent, said compositionoptionally further comprising a biologically effective amount of atleast one additional biologically active compound or agent.
 11. Thecomposition of claim 10 wherein the at least one additional biologicallyactive compound or agent is selected from insecticides of the groupconsisting of sodium channel modulators, cholinesterase inhibitors,neonicotinoids, insecticidal macrocyclic lactones, GABA-regulatedchloride channel blockers, chitin synthesis inhibitors, juvenile hormonemimics, octopamine receptor ligands, ecdysone agonists, ryanodinereceptor ligands, nereistoxin analogs, mitochondrial electron transportinhibitors, lipid biosynthesis inhibitors, cyclodiene insecticides,molting inhibitors, nucleopolyhedrovirus, a member of Bacillusthuringiensis, an encapsulated delta-endotoxin of Bacillus thuringiensisand a naturally occurring or a genetically modified viral insecticide.12. The composition of claim 10 wherein the at least one additionalbiologically active compound or agent is selected from the groupconsisting of abamectin, acephate, acetamiprid, acetoprole, aldicarb,amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl,bifenthrin, bifenazate, bistrifluoron, buprofezin, carbofuran, cartap,chinomethionat, chlorfenapyr, chlorfluazuron, chlorantraniliprole,chlorpyrifos, chlorpyrifos-methyl, chlorobenzilate, chromafenozide,clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin,gamma-cyhalothrin, lambda-cyhalothrin, cyhexatin, cypermethrin,cyromazine, deltamethrin, diafenthiuron, diazinon, dicofol, dieldrin,dienochlor, diflubenzuron, dimefluthrin, dimethoate, dinotefuran,diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etoxazole,fenamiphos, fenazaquin, fenbutatin oxide, fenothiocarb, fenoxycarb,fenpropathrin, fenpyroximate, fenvalerate, fipronil, flonicamid,flubendiamide, flucythrinate, tau-fluvalinate, flufenerim, flufenoxuron,fonophos, halofenozide, hexaflumuron, hexythiazox, hydramethylnon,imicyafos, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion,metaflumizone, metaldehyde, methamidophos, methidathion, methomyl,methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos,nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion,parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon,pirimicarb, profenofos, profluthrin, propargite, protrifenbute,pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl,pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine,spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat,sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin,terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb,thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus, an encapsulateddelta-endotoxin of Bacillus thuringiensis, baculovirus, entomopathogenicbacteria, entomopathogenic virus and entomopathogenic fungi.
 13. Thecomposition of claim 12 wherein the at least one additional biologicallyactive compound or agent is selected from the group consisting ofabamectin, acetamiprid, amitraz, avermectin, azadirachtin, bifenthrin,buprofezin, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos,clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, dieldrin,dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate,ethiprole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid,flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, imidacloprid,indoxacarb, lufenuron, metaflumizone, methomyl, methoprene,methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine,pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram,spinosad, spirodiclofen, spiromesifen, tebufenozide, thiacloprid,thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate,triflumuron, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki, nucleopolyhedrovirus and an encapsulateddelta-endotoxin of Bacillus thuringiensis.
 14. The composition of claim10 in the form of a soil drench liquid formulation.
 15. A spraycomposition for controlling an invertebrate pest, comprising: (a) abiologically effective amount of the compound of claim 1 or thecomposition of claim 10; and (b) a propellant.
 16. A bait compositionfor controlling an invertebrate pest, comprising: (a) a biologicallyeffective amount of the compound of claim 1 or the composition of claim10; (b) one or more food materials; (c) optionally an attractant; and(d) optionally a humectant.
 17. A trap device for controlling aninvertebrate pest, comprising: (a) the bait composition of claim 16; and(b) a housing adapted to receive the bait composition, wherein thehousing has at least one opening sized to permit the invertebrate pestto pass through the opening so the invertebrate pest can gain access tothe bait composition from a location outside the housing, and whereinthe housing is further adapted to be placed in or near a locus ofpotential or known activity for the invertebrate pest.
 18. A method forcontrolling an invertebrate pest comprising contacting the invertebratepest or its environment with a biologically effective amount of acompound of claim
 1. 19. A method for controlling an invertebrate pestcomprising contacting the invertebrate pest or its environment with acomposition of claim
 10. 20. The method of claim 19 wherein theenvironment is soil and the composition is applied to the soil as a soildrench formulation.
 21. A method for controlling a cockroach, an ant ora termite, comprising contacting a cockroach, an ant, or a termite withthe bait composition in a trap device of claim
 17. 22. A method forcontrolling a mosquito, a black fly, a stable, fly, a deer fly, a horsefly, a wasp, a yellow jacket, a hornet, a tick, a spider, an ant, or agnat, comprising contacting a mosquito, a black fly, a stable, fly, adeer fly, a horse fly, a wasp, a yellow jacket, a hornet, a tick, aspider, an ant, or a gnat with the spray composition of claim 15dispensed from a spray container.
 23. A method for protecting a seedfrom an invertebrate pest comprising contacting the seed with abiologically effective amount of a compound of claim
 1. 24. The methodof claim 23 wherein the seed is coated with the compound of claim 1formulated as a composition comprising a film former or adhesive agent.25. A treated seed comprising a compound of claim 1 in an amount of fromabout 0.0001 to 1% by weight of the seed before treatment.
 26. Acomposition for protecting an animal from an invertebrate parasitic pestcomprising a parasiticidally effective amount of a compound of claim 1and at least one carrier.
 27. The composition of claim 26 in a form fororal administration.
 28. A method for protecting an animal from aninvertebrate parasitic pest comprising administering to the animal aparasiticidally effective amount of a compound of claim 1.